| Ridgefield 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1679 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | 2:30 pm | |
| TBA | JV Baseball | Joel Barlow | Home - East Ridge MS [Directions] | TBA | ||
| TBA | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | TBA | 2:30 pm | |
| TBA | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | TBA | 8:30 am | |
| TBA | JV Football | Trumbull | Home - Tiger Hollow Stadium [Directions] | TBA | ||
| TBA | JV Boys Golf | New Canaan | Home - Silver Spring GC [Directions] | TBA | ||
| TBA | JV Boys Golf | Fairfield Ludlowe | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | TBA | ||
| TBA | JV Boys Golf | Staples | Home - Silver Spring GC [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Fairfield Prep | Home - Danbury Ice Arena [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Briarcliff (NY) | Home - Tiger Hollow Turf Field II [Directions] | TBA | ||
| TBA | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | TBA | 2:30 pm | |
| TBA | V Boys Rugby | Southington | Away [Directions] | TBA | ||
| TBA | JV Boys Soccer | New Canaan | Home - Lower Grass Field [Directions] | TBA | ||
| TBA | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | TBA | 2:30 pm | |
| TBA | JV Boys Tennis | Fairfield Ludlowe | Home - Yanity Tennis Courts [Directions] | TBA | ||
| TBA | JV Boys Tennis | Wilton | Home - Yanity Tennis Courts [Directions] | TBA | ||
| TBA | FR Girls Basketball | Weston | Home - RHS Main Gym [Directions] | TBA | ||
| TBA | JV Field Hockey | Westhill | Home - Tiger Hollow Stadium [Directions] | TBA | ||
| TBA | FR Field Hockey | Westhill | Away - Westhill Football Field [Directions] | TBA | 2:30 pm | |
| TBA | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | TBA | 2 pm | |
| TBA | V Girls Tennis | Bridgeport Central | Home - RHS Tennis Courts [Directions] | W Forfeit | ||
| TBA | JV Girls Tennis | Greenwich | Home - Yanity Tennis Courts [Directions] | TBA | ||
| TBA | JV Girls Tennis | Staples | Home - Yanity Tennis Courts [Directions] | TBA | ||
| TBA | JV Girls Tennis | Fairfield Ludlowe | Home - Yanity Tennis Courts [Directions] | TBA | ||
| TBA | V Girls Volleyball | JJ Play Day | Away | 4:00 p.m. | cancelled | |
| Sun., 7/1 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Mon., 7/2 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Mon., 7/2 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:00 a.m.-3pm | ||
| Mon., 7/2 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Scotts Ridge MS Turf [Directions] | 5:30 p.m.-7:30pm | ||
| Tue., 7/3 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Tue., 7/3 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:00 a.m.-3pm | ||
| Wed., 7/4 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Wed., 7/4 | School Holidays and Closings | Independence Day | ||||
| Thu., 7/5 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Thu., 7/5 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:00 a.m.-3pm | ||
| Thu., 7/5 | Miscellaneous Events | SCOR 8v8 (Girls) | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-5pm | ||
| Fri., 7/6 | Miscellaneous Events | FIELD CLOSED FOR FIREWORKS PREP | - Tiger Hollow Stadium | 12:00 a.m.-12pm | ||
| Fri., 7/6 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:00 a.m.-3pm | ||
| Mon., 7/9 | Miscellaneous Events | RYF Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Mon., 7/9 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Mon., 7/9 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Scotts Ridge MS Turf [Directions] | 5:30 p.m.-7:30pm | ||
| Tue., 7/10 | Miscellaneous Events | Youth Field Hockey Camp | - Tiger Hollow Stadium | 8:30 a.m.-11:30am | ||
| Tue., 7/10 | Miscellaneous Events | RYF Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Tue., 7/10 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 7/10 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Wed., 7/11 | Miscellaneous Events | Youth Field Hockey Camp | - Tiger Hollow Stadium | 8:30 a.m.-11:30am | ||
| Wed., 7/11 | Miscellaneous Events | RYF Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Wed., 7/11 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Wed., 7/11 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m.-7:30pm | ||
| Wed., 7/11 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Tiger Hollow Turf Field II [Directions] | 5:30 p.m.-7:30pm | ||
| Thu., 7/12 | Miscellaneous Events | Youth Field Hockey Camp | - Tiger Hollow Stadium | 8:30 a.m.-11:30am | ||
| Thu., 7/12 | Miscellaneous Events | RYF Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Thu., 7/12 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 7/12 | Miscellaneous Events | SCOR 8v8 (Girls) | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-5pm | ||
| Thu., 7/12 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Fri., 7/13 | Miscellaneous Events | Youth Field Hockey Camp | - Tiger Hollow Stadium | 8:30 a.m.-11:30am | ||
| Fri., 7/13 | Miscellaneous Events | RYF Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Fri., 7/13 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Fri., 7/13 | Miscellaneous Events | Running Club Meet | Home - Tiger Hollow Stadium [Directions] | 6:30 p.m.-8:00pm | ||
| Sun., 7/15 | Miscellaneous Events | RYL Alumni Game | Home - Tiger Hollow Stadium [Directions] | 11:00 a.m.-3pm | ||
| Sun., 7/15 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 7/16 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Mon., 7/16 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Scotts Ridge MS Turf [Directions] | 5:30 p.m.-7:30pm | ||
| Tue., 7/17 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 7/17 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Wed., 7/18 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Wed., 7/18 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m.-7:30pm | ||
| Wed., 7/18 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Tiger Hollow Turf Field II [Directions] | 5:30 p.m.-7:30pm | ||
| Thu., 7/19 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 7/19 | Miscellaneous Events | SCOR 8v8 (Girls) | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-5pm | ||
| Thu., 7/19 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Fri., 7/20 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Fri., 7/20 | Miscellaneous Events | Running Club Meet | Home - Tiger Hollow Stadium [Directions] | 6:30 p.m.-8:00pm | ||
| Sun., 7/22 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 7/23 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Mon., 7/23 | Miscellaneous Events | Westchester Elite Lacrosse | Home - Scotts Ridge MS Turf [Directions] | 5:30 p.m.-7:30pm | ||
| Tue., 7/24 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 7/24 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Wed., 7/25 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 7/26 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 7/26 | Miscellaneous Events | SCOR 8v8 (Girls) | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-5pm | ||
| Thu., 7/26 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Fri., 7/27 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Sun., 7/29 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 7/30 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 7/31 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 7/31 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Wed., 8/1 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 8/2 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 8/2 | Miscellaneous Events | SCOR 8v8 (Girls) | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-5pm | ||
| Thu., 8/2 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Fri., 8/3 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Fri., 8/3 | Miscellaneous Events | Running Club Meet | Home - Tiger Hollow Stadium [Directions] | 6:30 p.m.-8:00pm | ||
| Sun., 8/5 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 8/6 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Mon., 8/6 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Mon., 8/6 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 8/7 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Tue., 8/7 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Tue., 8/7 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Tue., 8/7 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Wed., 8/8 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Wed., 8/8 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Wed., 8/8 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 8/9 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Thu., 8/9 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Thu., 8/9 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Thu., 8/9 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 6:30 p.m.-8:30pm | ||
| Fri., 8/10 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Fri., 8/10 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Fri., 8/10 | Miscellaneous Events | RBA Camp | - RHS Main and Aux Gyms | 8:30 a.m.-2:30pm | ||
| Sat., 8/11 | Miscellaneous Events | Ryan Meegan Memorial Alumni Game | - Tiger Hollow Stadium | 4:00 p.m.-8:00pm | ||
| Sun., 8/12 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 8/13 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Mon., 8/13 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Mon., 8/13 | Miscellaneous Events | Ridgefield Youth Volleyball | - RHS Main Gym | 9:00 a.m.-1:00pm | ||
| Tue., 8/14 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Tue., 8/14 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Tue., 8/14 | Miscellaneous Events | Ridgefield Youth Volleyball | - RHS Main Gym | 9:00 a.m.-1:00pm | ||
| Tue., 8/14 | Miscellaneous Events | Ridgefield Youth Field Hockey Camp | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Wed., 8/15 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Wed., 8/15 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Wed., 8/15 | Miscellaneous Events | Ridgefield Youth Volleyball | - RHS Main Gym | 9:00 a.m.-1:00pm | ||
| Wed., 8/15 | Miscellaneous Events | Ridgefield Youth Field Hockey Camp | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Thu., 8/16 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Thu., 8/16 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Thu., 8/16 | Miscellaneous Events | Ridgefield Youth Volleyball | - RHS Main Gym | 9:00 a.m.-1:00pm | ||
| Thu., 8/16 | Miscellaneous Events | Ridgefield Youth Field Hockey Camp | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Fri., 8/17 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:00pm | ||
| Fri., 8/17 | Miscellaneous Events | SCOR Camp | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:00pm | ||
| Fri., 8/17 | Miscellaneous Events | Ridgefield Youth Volleyball | - RHS Main Gym | 9:00 a.m.-1:00pm | ||
| Fri., 8/17 | Miscellaneous Events | Ridgefield Youth Field Hockey Camp | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Mon., 8/20 | Miscellaneous Events | RYFH Clinic | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Mon., 8/20 | School Holidays and Closings | Fall Sports Kick Off Meeting for Parents and Students | ||||
| Tue., 8/21 | Miscellaneous Events | RYFH Clinic | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m.-5pm | ||
| Tue., 8/21 | Miscellaneous Events | RYF | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m.-8pm | ||
| Wed., 8/22 | V Football | Brookfield (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Wed., 8/22 | Miscellaneous Events | RYFH Clinic | Home - RHS Upper Grass Field [Directions] | 3:00 p.m.-5pm | ||
| Sat., 8/25 | V Football | Fairfield Prep (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Sat., 8/25 | FR Football | Fairfield Prep (Scrim.) | Away - Barlow Field, Fairfield University [Directions] | 1:00 p.m. | 10:30 am | |
| Sat., 8/25 | School Holidays and Closings | SAT Test | ||||
| Mon., 8/27 | V Boys Soccer | Hamden (Scrim.) | Away - HHS Turf Field #2 [Directions] | 5:00 p.m. | 3 pm | |
| Mon., 8/27 | V Girls Soccer | Brookfield (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Mon., 8/27 | JV Girls Soccer | Brookfield (Scrim.) | Home - Tiger Hollow Turf Field II [Directions] | 10:00 a.m. | ||
| Mon., 8/27 | Miscellaneous Events | RYFH | Home - Tiger Hollow Stadium [Directions] | 6:00 p.m.-8pm | ||
| Tue., 8/28 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 7:00 p.m. | 5:30 pm | |
| Tue., 8/28 | V Girls Soccer | New Fairfield (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 1:30 p.m. | ||
| Tue., 8/28 | JV Girls Soccer | New Fairfield (Scrim.) | Home - Tiger Hollow Turf Field II [Directions] | 1:30 p.m. | ||
| Tue., 8/28 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 8/30 | V Field Hockey | John Jay (NY) (Scrim.) | Away | 3:30 p.m. | 2:30 pm | |
| Thu., 8/30 | JV Field Hockey | John Jay (NY) (Scrim.) | Away | 3:30 p.m. | 2:30 pm | |
| Thu., 8/30 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 8/30 | School Holidays and Closings | First Day of School Grades K-9 | ||||
| Fri., 8/31 | V Football | Newtown (Scrim.) | Away - Blue and Gold Stadium [Directions] | 5:30 p.m. | 3 pm | |
| Fri., 8/31 | FR Football | Newtown (Scrim.) | Away - Blue and Gold Stadium [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 8/31 | V Girls Soccer | New Milford (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Fri., 8/31 | JV Girls Soccer | New Milford (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Fri., 8/31 | V Girls Volleyball | Weston (Scrim.) | Home - RHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 8/31 | JV Girls Volleyball | Weston (Scrim.) | Home - RHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 8/31 | FR Girls Volleyball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:30 p.m. | 2:30 pm | |
| Fri., 8/31 | School Holidays and Closings | First Day of School Grades 10-12 | ||||
| Sat., 9/1 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 6:00 p.m.-8:00 p.m. | ||
| Sun., 9/2 | V Boys Soccer | Newtown (Scrim.) | Away - Blue and Gold Stadium [Directions] | 6:00 p.m. | 4:30 pm | |
| Sun., 9/2 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-3:30pm | ||
| Mon., 9/3 | School Holidays and Closings | Labor Day | School closed | |||
| Tue., 9/4 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 9/4 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 9/5 | V Girls Volleyball | Val Dickinson Jamboree at Staples HS | Away [Directions] | 3:30 p.m. | 2:30 pm | |
| Wed., 9/5 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/6 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/6 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 9/7 | V Football | Darien | Away - DHS Stadium Field [Directions] | L 6-30 | 5 pm | |
| Fri., 9/7 | V Sideline Cheerleading | Darien | Away - DHS Stadium Field [Directions] | 7:00 p.m. | 5:30pm | |
| Fri., 9/7 | V Field Hockey | New Fairfield | Home - Tiger Hollow Stadium [Directions] | W 3-0 | ||
| Fri., 9/7 | JV Field Hockey | New Fairfield | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Volleyball | Pomperaug | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/7 | JV Girls Volleyball | Pomperaug | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 9/8 | JV Football | Darien | Home - Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/8 | FR Football | Darien | Home - Tiger Hollow II [Directions] | 10:30 a.m. | ||
| Sat., 9/8 | V Boys Soccer | Trinity Catholic | Home - Tiger Hollow Stadium [Directions] | W 6-1 | ||
| Sat., 9/8 | JV Sideline Cheerleading | Darien | Home - Tiger Hollow Turf Field II [Directions] | 10:30 a.m. | ||
| Sat., 9/8 | V Girls Soccer | Trinity Catholic | Away | W 6-0 | 9:15 am | |
| Sat., 9/8 | School Holidays and Closings | ACT Test | ||||
| Sun., 9/9 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 9/9 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-4pm | ||
| Sun., 9/9 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-4pm | ||
| Sun., 9/9 | School Holidays and Closings | Rosh Hashana begins at sundown | ||||
| Mon., 9/10 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 9/10 | School Holidays and Closings | Rosh Hashana | School closed | |||
| Tue., 9/11 | V Boys Cross Country | Westhill, Darien, Stamford | Home - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | Westhill, Darien, Stamford | Home - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 5-0 | 2:30 pm | |
| Tue., 9/11 | JV Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 5:30 p.m. | 4 pm | |
| Tue., 9/11 | FR Field Hockey | Danbury | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 6-0 | 2:30 pm | |
| Tue., 9/11 | JV Girls Soccer | Stamford | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Greenwich | Home - RHS Main Gym [Directions] | W 3-2 | ||
| Tue., 9/11 | JV Girls Volleyball | Greenwich | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 9/11 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 9/11 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 9/12 | V Boys Soccer | Stamford | Home - Tiger Hollow Stadium [Directions] | W 3-2 | ||
| Wed., 9/12 | JV Boys Soccer | Stamford | Home - Lower Grass Field [Directions] | W 1-0 | ||
| Wed., 9/12 | FR Boys Soccer | Stamford | Away [Directions] | W 4-0 | 2:30 pm | |
| Wed., 9/12 | V Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - RHS Main Gym [Directions] | L 0-3 | ||
| Wed., 9/12 | JV Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - RHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/12 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/13 | FR Football | Stamford | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 9/13 | V Girls Soccer | Trumbull | Home - Tiger Hollow Stadium [Directions] | W 2-0 | ||
| Thu., 9/13 | JV Girls Soccer | Trumbull | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | FR Girls Soccer | Trumbull | Away - Field 9 [Directions] | 3:15 p.m. | 1:30 pm | |
| Thu., 9/13 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/13 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 9/13 | School Holidays and Closings | RHS Open House | ||||
| Thu., 9/13 | School Holidays and Closings | Early dismissal for students - PD for staff | ||||
| Fri., 9/14 | V Football | Stamford | Home - Tiger Hollow Stadium [Directions] | W 42-12 | ||
| Fri., 9/14 | V Boys Soccer | Trumbull | Away - New Turf Field [Directions] | L 2-6 | 2:30 pm | |
| Fri., 9/14 | JV Boys Soccer | Trumbull | Away - The Pit [Directions] | L 2-3 | 2:30 pm | |
| Fri., 9/14 | FR Boys Soccer | Trumbull | Home - Lower Grass Field [Directions] | W 2-1 | ||
| Fri., 9/14 | V Sideline Cheerleading | Stamford | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/14 | Fall Dance Team | Stamford | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/14 | V Field Hockey | Stamford | Home - Tiger Hollow Stadium [Directions] | W 3-1 | ||
| Fri., 9/14 | V Girls Volleyball | Trinity Catholic | Home - RHS Main Gym [Directions] | W 3-1 | ||
| Fri., 9/14 | JV Girls Volleyball | Trinity Catholic | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 9/15 | JV Football | Stamford | Away [Directions] | 10:30 a.m. | 8:30 am | |
| Sat., 9/15 | JV Field Hockey | Stamford | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | V Girls Soccer | Danbury | Home - Tiger Hollow Stadium [Directions] | W 6-0 | ||
| Sat., 9/15 | JV Girls Soccer | Danbury | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 10:30 a.m. | 9 am | |
| Sat., 9/15 | Miscellaneous Events | RYFH | Home [Directions] | 10:30 a.m.-12:00pm | ||
| Sun., 9/16 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 10:00 a.m.-1:00pm | ||
| Sun., 9/16 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 9/16 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Sun., 9/16 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 2:30 p.m.-5:30 p.m. | ||
| Mon., 9/17 | V Boys Cross Country | Wilton, Brien McMahon, Norwalk | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 9/17 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | L 1-5 | 2:30 pm | |
| Mon., 9/17 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | L 0-1 | 2:30 pm | |
| Mon., 9/17 | FR Boys Soccer | Danbury | Home - Lower Grass Field [Directions] | W 6-2 | ||
| Mon., 9/17 | V Girls Cross Country | Wilton, Brien McMahon, Norwalk | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 9/17 | V Field Hockey | Fairfield Warde | Away - Tomlinson MS [Directions] | T 2-2 | 2:30 pm | |
| Mon., 9/17 | JV Field Hockey | Fairfield Warde | Away - Tomlinson MS [Directions] | 5:30 p.m. | 3:45 pm | |
| Mon., 9/17 | V Girls Volleyball | Stamford | Home - RHS Main Gym [Directions] | W 3-2 | ||
| Mon., 9/17 | JV Girls Volleyball | Stamford | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | FR Girls Volleyball | Stamford | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 9/17 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 9/17 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 9/18 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | L 2-3 | 2:30 pm | |
| Tue., 9/18 | JV Girls Volleyball | Weston | Away - WHS Old Gymnasium [Directions] | 3:30 p.m. | 2:30 pm | |
| Tue., 9/18 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Away | 4:00 p.m. | 2:30 pm | |
| Tue., 9/18 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 9/18 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Tue., 9/18 | School Holidays and Closings | Yom Kippur begins at sundown | ||||
| Wed., 9/19 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 9/19 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Wed., 9/19 | School Holidays and Closings | Yom Kippur | School closed | |||
| Thu., 9/20 | FR Football | Bridgeport Central | Home - Tiger Hollow II [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | W 2-0 | 4:45 pm | |
| Thu., 9/20 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 9/20 | FR Girls Soccer | Fairfield Ludlowe | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | 2:30 pm | |
| Thu., 9/20 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Thu., 9/20 | FR Girls Volleyball | Trumbull | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/20 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 9/21 | V Boys Soccer | Fairfield Ludlowe | Home - Tiger Hollow Stadium [Directions] | L 0-3 | ||
| Fri., 9/21 | JV Boys Soccer | Fairfield Ludlowe | Home - Lower Grass Field [Directions] | L 1-2 | ||
| Fri., 9/21 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | W 1-0 | 2:30 pm | |
| Fri., 9/21 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 7:00 p.m. | 5:30 pm | |
| Fri., 9/21 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 9/22 | V Football | Bridgeport Central | Home - Tiger Hollow Stadium [Directions] | W 51-0 | ||
| Sat., 9/22 | V Sideline Cheerleading | Bridgeport Central | Home - Tiger Hollow Stadium [Directions] | 3:00 p.m. | ||
| Sat., 9/22 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | OT-L 3-4 | 8:30 am | |
| Sat., 9/22 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 11:30 a.m. | 10 am | |
| Sat., 9/22 | FR Field Hockey | Wilton | Home - Tiger Hollow Turf Field II [Directions] | 10:00 a.m. | ||
| Sat., 9/22 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | W 2-0 | 10:00am | |
| Sat., 9/22 | JV Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 12:00 p.m. | 10:30 pm | |
| Sat., 9/22 | Miscellaneous Events | RYF | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m.-10pm | Will start when Varsity football ends | |
| Sun., 9/23 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 9/23 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Sun., 9/23 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-4pm | ||
| Mon., 9/24 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:30 p.m. | 2:30 pm | |
| Mon., 9/24 | V Boys Soccer | Greenwich | Home - Tiger Hollow Stadium [Directions] | L 1-3 | ||
| Mon., 9/24 | JV Boys Soccer | Greenwich | Home - Lower Grass Field [Directions] | L 3-4 | ||
| Mon., 9/24 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:00 pm | Diving @ New Canaan YMCA-3PM |
| Mon., 9/24 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 3-0 | 2:30 pm | |
| Mon., 9/24 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Mon., 9/24 | FR Girls Volleyball | Danbury | Away - DHS [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 9/24 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 9/24 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 9/25 | V Girls Soccer | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | W 3-0 | ||
| Tue., 9/25 | JV Girls Soccer | Brien McMahon | Home - Lower Grass Field [Directions] | Cancelled | ||
| Tue., 9/25 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 9/25 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 9/26 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | L 1-3 | 4:45 pm | |
| Wed., 9/26 | JV Boys Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | W 2-0 | 2:30 pm | |
| Wed., 9/26 | FR Boys Soccer | Brien McMahon | Home - Lower Grass Field [Directions] | W 4-1 | ||
| Wed., 9/26 | V Field Hockey | Westhill | Home - Tiger Hollow Stadium [Directions] | W 3-1 | ||
| Wed., 9/26 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:30 p.m. | 2:30 pm | |
| Wed., 9/26 | V Girls Volleyball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | L 0-3 | Dig Pink match | |
| Wed., 9/26 | JV Girls Volleyball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 5:15 p.m. | Dig Pink match | |
| Wed., 9/26 | FR Girls Volleyball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 4:00 p.m. | Dig Pink match | |
| Wed., 9/26 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 9/26 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Thu., 9/27 | V Boys Cross Country | Fairfield Warde, St. Joseph, Trinity Catholic | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 pm | at St Joseph |
| Thu., 9/27 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:15 p.m. | 4:30 pm | |
| Thu., 9/27 | FR Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | L 1-4 | 2:45 pm | |
| Thu., 9/27 | V Girls Cross Country | Fairfield Warde, St. Joseph, Trinity Catholic | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 pm | at St Joseph |
| Thu., 9/27 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 5-2 | 5 pm | |
| Thu., 9/27 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | 3:30 pm | |
| Thu., 9/27 | FR Field Hockey | Norwalk | Home - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Bridgeport Central | Home - Tiger Hollow Stadium [Directions] | W 6-0 | ||
| Thu., 9/27 | FR Girls Soccer | Greenwich | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 9/27 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 9/28 | V Football | Staples | Home - Tiger Hollow Stadium [Directions] | L 17-35 | ||
| Fri., 9/28 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 2-1 | 2:30 pm | |
| Fri., 9/28 | JV Boys Soccer | Bridgeport Central | Away - Seaside Park [Directions] | W 4-1 | 2:30 pm | |
| Fri., 9/28 | V Sideline Cheerleading | Staples | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/28 | Fall Dance Team | Staples | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/28 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | 2:45 pm | |
| Fri., 9/28 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 9/29 | V Girls Soccer | Darien | Home - Tiger Hollow Stadium [Directions] | W 2-0 | ||
| Sat., 9/29 | JV Girls Soccer | Darien | Home - Tiger Hollow Stadium [Directions] | 1:00 p.m. | ||
| Sat., 9/29 | FR Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 9/29 | V Girls Volleyball | John Jay Invitational | Away | TBA | 7:45 am | |
| Sat., 9/29 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 9:00 a.m.-10:30am | ||
| Sat., 9/29 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 1:00 p.m.-5pm | ||
| Sat., 9/29 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 5:00 p.m.-8:30pm | ||
| Sat., 9/29 | Miscellaneous Events | RYF | - Tiger Hollow Stadium | 6:30 p.m.-9:00pm | ||
| Sun., 9/30 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 11:00 a.m.-2pm | ||
| Sun., 9/30 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 9/30 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Mon., 10/1 | V Boys Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | L 1-2 | 2:30 pm | |
| Mon., 10/1 | JV Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | W 2-1 | 2:30 pm | |
| Mon., 10/1 | FR Boys Soccer | Darien | Home - Lower Grass Field [Directions] | W 4-0 | ||
| Mon., 10/1 | V Field Hockey | New Canaan | Home - Tiger Hollow Stadium [Directions] | L 0-2 | ||
| Mon., 10/1 | JV Field Hockey | New Canaan | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Mon., 10/1 | FR Field Hockey | New Canaan | Away - WTT2 [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 10/1 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-1 | 2:30 pm | |
| Mon., 10/1 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 10/1 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - RHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/1 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 10/1 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 10/2 | V Boys Cross Country | Greenwich, Danbury, Staples | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/2 | V Girls Cross Country | Greenwich, Danbury, Staples | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/2 | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/2 | FR Girls Soccer | Wilton | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 10/2 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 10/3 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 1-0 | 4:45 pm | |
| Wed., 10/3 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | 3 pm | |
| Wed., 10/3 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | 2:30 pm | |
| Wed., 10/3 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 10/3 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 10/3 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 10/3 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Thu., 10/4 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 10/4 | V Boys Soccer | Wilton | Home - Tiger Hollow Stadium [Directions] | T 2-2 | ||
| Thu., 10/4 | JV Boys Soccer | Wilton | Home - Lower Grass Field [Directions] | L 1-2 | ||
| Thu., 10/4 | FR Boys Soccer | Wilton | Away [Directions] | L 0-1 | 2:30 pm | |
| Thu., 10/4 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 10/4 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 10/4 | Miscellaneous Events | Sportsmanship Conference | Away | TBA | Yes | event ends at 12:30 pm |
| Fri., 10/5 | V Football | St. Joseph | Home - Tiger Hollow Stadium [Directions] | L 0-42 | ||
| Fri., 10/5 | V Sideline Cheerleading | St. Joseph | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/5 | Fall Dance Team | St. Joseph | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/5 | V Field Hockey | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | W 3-1 | ||
| Fri., 10/5 | JV Field Hockey | Brien McMahon | Home - Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Westhill/Stamford | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 2:30 pm | |
| Fri., 10/5 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Fri., 10/5 | FR Girls Volleyball | Darien | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 10/6 | JV Football | St. Joseph | Away - St. Joseph HS [Directions] | 2:00 p.m. | 11:30 am | |
| Sat., 10/6 | Miscellaneous Events | SCOR Tournament | - Tiger Hollow Stadium | 8:00 a.m.-6pm | ||
| Sat., 10/6 | Miscellaneous Events | SCOR Tournament | - Tiger Hollow Turf Field II | 8:00 a.m.-6pm | ||
| Sat., 10/6 | Miscellaneous Events | SCOR Tournament | - RHS Lower Grass Field | 8:00 a.m.-6pm | ||
| Sat., 10/6 | School Holidays and Closings | SAT Test | ||||
| Sun., 10/7 | Miscellaneous Events | SCOR Tournament | - Tiger Hollow Stadium | 8:00 a.m.-6pm | ||
| Sun., 10/7 | Miscellaneous Events | SCOR Tournament | - Tiger Hollow Turf Field II | 8:00 a.m.-6pm | ||
| Sun., 10/7 | Miscellaneous Events | SCOR Tournament | - RHS Lower Grass Field | 8:00 a.m.-6pm | ||
| Mon., 10/8 | Miscellaneous Events | RBA | Home - RHS Main Gym [Directions] | 4:00 p.m.-8pm | ||
| Mon., 10/8 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 10/8 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Mon., 10/8 | School Holidays and Closings | Columbus Day | School closed | |||
| Tue., 10/9 | V Boys Cross Country | New Canaan, Trumbull, Fairfield Ludlowe | Home - Upper Grass Field [Directions] | 4:00 p.m. | Senior Day | |
| Tue., 10/9 | V Girls Cross Country | New Canaan, Trumbull, Fairfield Ludlowe | Home - Upper Grass Field [Directions] | 4:00 p.m. | Senior Day | |
| Tue., 10/9 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | W 3-0 | 3:00 pm | |
| Tue., 10/9 | JV Field Hockey | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/9 | V Girls Soccer | Staples | Home - Tiger Hollow Stadium [Directions] | T 0-0 | ||
| Tue., 10/9 | JV Girls Soccer | Staples | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/9 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 10/9 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 10/10 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 1-4 | 2:30 pm | |
| Wed., 10/10 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | L 1-3 | 2:30 pm | |
| Wed., 10/10 | FR Boys Soccer | Staples | Home - Lower Grass Field [Directions] | L 1-4 | ||
| Wed., 10/10 | FR Field Hockey | Fairfield Ludlowe | Home - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Girls Volleyball | Wilton | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/10 | JV Girls Volleyball | Wilton | Home - RHS Main Gym [Directions] | 5:45 p.m. | ||
| Wed., 10/10 | FR Girls Volleyball | Wilton | Home - RHS Aux Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 10/10 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Wed., 10/10 | School Holidays and Closings | College Fair at Wilton HS | ||||
| Thu., 10/11 | V Field Hockey | Trumbull | Home - Tiger Hollow Stadium [Directions] | W 2-0 | ||
| Thu., 10/11 | JV Field Hockey | Trumbull | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Thu., 10/11 | V Girls Swimming and Diving | Fairfield Warde | Home - Pool at Barlow Mountain School [Directions] | 1:30 p.m. | ||
| Thu., 10/11 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 10/11 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 10/11 | School Holidays and Closings | Early dismissal for students - PD for staff | ||||
| Fri., 10/12 | V Boys Soccer | St. Joseph | Home - Tiger Hollow Stadium [Directions] | W 2-1 | Senior Night | |
| Fri., 10/12 | JV Boys Soccer | St. Joseph | Home - Tiger Hollow Stadium [Directions] | W 3-0 | ||
| Fri., 10/12 | FR Field Hockey | Trumbull | Away - New Turf Field [Directions] | 7:15 p.m. | 5:15 pm | |
| Fri., 10/12 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 10/13 | V Boys Cross Country | Manhattan College Invitational | Away | TBA | ||
| Sat., 10/13 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 0-2 | 1 pm | |
| Sat., 10/13 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 1:30 p.m. | 12 pm | |
| Sat., 10/13 | FR Field Hockey | Greenwich | Home - Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | L 1-0 | 1:30 pm | |
| Sat., 10/13 | FR Girls Soccer | New Canaan | Home - Tiger Hollow Turf Field II [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 2:00 p.m.-5pm | ||
| Sat., 10/13 | Miscellaneous Events | RYF | Home - Tiger Hollow Stadium [Directions] | 3:30 p.m.-8:30 p.m. | ||
| Sat., 10/13 | School Holidays and Closings | PSAT Test | ||||
| Sun., 10/14 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 10/14 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Sun., 10/14 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 2:00 p.m.-4pm | ||
| Mon., 10/15 | V Boys Soccer | New Canaan | Home - Tiger Hollow Stadium [Directions] | L 0-2 | ||
| Mon., 10/15 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | L 2-1 | 2 pm | |
| Mon., 10/15 | V Girls Swimming and Diving | Staples | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | 2:30 pm | |
| Mon., 10/15 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 10/15 | FR Girls Volleyball | Staples | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 10/15 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 10/16 | V Field Hockey | St. Joseph | Home - Tiger Hollow Stadium [Directions] | W 1-0 | Senior Night | |
| Tue., 10/16 | JV Field Hockey | St. Joseph | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 6-0 | 5:15 pm | |
| Tue., 10/16 | JV Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:15 p.m. | 3:30 pm | |
| Tue., 10/16 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 10/16 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 10/17 | FR Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | T 3-3 | 3 pm | |
| Wed., 10/17 | JV Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 6:30 p.m. | 4:30 pm | |
| Wed., 10/17 | V Girls Volleyball | St. Joseph | Home - RHS Main Gym [Directions] | W 3-2 | ||
| Wed., 10/17 | JV Girls Volleyball | St. Joseph | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | FR Girls Volleyball | St. Joseph | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 10/17 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 10/17 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Cross Country Championships at Waveny Park, New Canaan | Away | 2:15 p.m. | 11:30 am | |
| Thu., 10/18 | FR Football | Wilton | Home - Tiger Hollow II [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Norwalk | Home - Tiger Hollow Stadium [Directions] | L 0-1 | ||
| Thu., 10/18 | JV Boys Soccer | Norwalk | Home - Lower Grass Field [Directions] | T 2-2 | ||
| Thu., 10/18 | V Girls Cross Country | FCIAC Cross Country Championships at Waveny Park, New Canaan | Away | 2:15 p.m. | 11:30 am | drop/pick |
| Thu., 10/18 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 10/18 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 10/19 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | L 0-2 | 2:30 pm | |
| Fri., 10/19 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | 4 pm | |
| Fri., 10/19 | FR Field Hockey | Darien | Home - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Westhill | Home - Tiger Hollow Stadium [Directions] | W 6-0 | Senior Night | |
| Fri., 10/19 | JV Girls Soccer | Westhill | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | New Canaan | Home - RHS Main Gym [Directions] | W 3-0 | SENIOR NIGHT | |
| Fri., 10/19 | JV Girls Volleyball | New Canaan | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | New Canaan | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/19 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 10/20 | V Football | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 21-6 | 11:30 am | |
| Sat., 10/20 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | L 5-0 | 10:30 am | |
| Sat., 10/20 | JV Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | W 1-0 | 8:30 am | |
| Sat., 10/20 | FR Boys Soccer | Westhill | Home - RHS Lower Grass Field [Directions] | L 1-2 | ||
| Sat., 10/20 | V Sideline Cheerleading | Wilton | Away - Nicholas Zeoli Field House [Directions] | 2:00 p.m. | 12:30 pm | |
| Sat., 10/20 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m.-5pm | ||
| Sun., 10/21 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 10:00 a.m.-4pm | ||
| Sun., 10/21 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 10/21 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Mon., 10/22 | JV Football | Wilton | Home - Tiger Hollow II [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 1-4 | 4:15 pm | |
| Mon., 10/22 | JV Sideline Cheerleading | Wilton | Home - Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | V Field Hockey | Staples | Home - Tiger Hollow Stadium [Directions] | OT-L 0-1 | ||
| Mon., 10/22 | JV Field Hockey | Staples | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 10/22 | V Girls Soccer | Fairfield Warde | Home - Tiger Hollow Stadium [Directions] | W 6-0 | ||
| Mon., 10/22 | JV Girls Soccer | Fairfield Warde | Home - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 10/22 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | 2:00 pm | |
| Mon., 10/22 | V Girls Volleyball | Norwalk | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/22 | JV Girls Volleyball | Norwalk | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 10/22 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 10/23 | V Boys Cross Country | Wilton Sub Varsity Meet | Away | TBA | 2:30 pm | |
| Tue., 10/23 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | T 1-1 | 2:30 pm | |
| Tue., 10/23 | V Girls Cross Country | Wilton Sub Varsity Meet | Away | TBA | 2:30 pm | 1 bus B/G XC |
| Tue., 10/23 | Miscellaneous Events | Powderpuff Football | Home - Tiger Hollow Stadium [Directions] | 6:00 p.m.-8pm | ||
| Tue., 10/23 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 10/23 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 10/24 | FR Boys Soccer | Fairfield Warde | Home - Lower Grass Field [Directions] | L 2-3 | ||
| Wed., 10/24 | JV Girls Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | 12:30 pm | |
| Wed., 10/24 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 0-3 | 2:30 pm | |
| Wed., 10/24 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 10/24 | FR Girls Volleyball | Westhill | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 10/25 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 10/25 | V Girls Soccer | Trumbull | Home [Directions] | W 4-0 | FCIAC Tourney Qtr Finals | |
| Thu., 10/25 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 10/25 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 10/26 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | 6:45 am | |
| Fri., 10/26 | V Football | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | W 24-6 | Homecoming | |
| Fri., 10/26 | V Boys Soccer | FCIAC Tournament Qtr Finals at higher seed | Away | 4:00 p.m. | ||
| Fri., 10/26 | V Sideline Cheerleading | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/26 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:50 a.m. | 6:45 am | |
| Fri., 10/26 | Fall Dance Team | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/26 | V Field Hockey | Darien | Away [Directions] | L 2-0 | 1:15 pm | dismiss at 1:05 pm |
| Fri., 10/26 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-0 | 2:30 pm | |
| Fri., 10/26 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/26 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/26 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 10/27 | JV Girls Swimming and Diving | JV FCIAC Championships @ TBA | Away | 2:30 p.m. | 12 pm | |
| Sat., 10/27 | JV Girls Volleyball | Girls JV Volleyball Invitational at Fairfield Warde | Away | 9:00 a.m. | 7:15 a.m. | drop off at Warde, return for pick up at 1 pm |
| Sat., 10/27 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 11:00 a.m.-1pm | ||
| Sat., 10/27 | Miscellaneous Events | RYFH | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12pm | ||
| Sat., 10/27 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 2:00 p.m.-5pm | ||
| Sat., 10/27 | School Holidays and Closings | ACT Test | ||||
| Sun., 10/28 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 11:30 a.m.-2:30 p.m. | ||
| Sun., 10/28 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 10/28 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Sun., 10/28 | Miscellaneous Events | RYFH | Home - Tiger Hollow Turf Field II [Directions] | 3:00 p.m.-4pm | ||
| Mon., 10/29 | V Boys Soccer | FCIAC Tournament Semi Finals | Away | TBA | ||
| Mon., 10/29 | V Field Hockey | FCIAC Semi Finals at Brien McMahon HS at 6 or 7:30 pm | Away | TBA | did not qualify | |
| Mon., 10/29 | V Girls Soccer | St. Joseph | Away [Directions] | W 2-1 | 3:15 pm | FCIAC Tourney Semi Finals at Wilton HS |
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving @ Westhill | Away | 5:00 p.m. | 2 pm | drop off only |
| Mon., 10/29 | Miscellaneous Events | Middle School XC Championship | Home - RHS Upper Grass Field [Directions] | 3:00 p.m.-6:00pm | ||
| Mon., 10/29 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 10/29 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 7:30 p.m.-9:00pm | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich | Away | 5:30 p.m. | 2:45 pm | |
| Tue., 10/30 | V Girls Volleyball | Trumbull | Away [Directions] | L 3-0 | 2:30 pm | |
| Tue., 10/30 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Tue., 10/30 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 10/31 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Wed., 10/31 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Wed., 10/31 | School Holidays and Closings | Halloween | ||||
| Thu., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 10 am | ED at 10:18 am |
| Thu., 11/1 | V Boys Soccer | FCIAC Tournament Finals at Norwalk HS | Away | 7:00 p.m. | ||
| Thu., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 10 am | ED at 10:18 am |
| Thu., 11/1 | V Field Hockey | FCIAC Finals at Brien McMahon HS | Away | 7:00 p.m. | did not qualify | |
| Thu., 11/1 | V Girls Soccer | New Canaan | Away [Directions] | W 1-0 | 5 pm | |
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Championships @ Greenwich | Away | 6:30 p.m. | 3:30 pm | |
| Thu., 11/1 | V Girls Volleyball | FCIAC Tournament Semi Finals at Ffld Ludlowe at 5 pm/7 pm | Away | TBA | did not qualify | |
| Thu., 11/1 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Thu., 11/1 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 11/2 | V Football | Greenwich | Home - Tiger Hollow Stadium [Directions] | L 3-33 | Senior Night | |
| Fri., 11/2 | V Sideline Cheerleading | Greenwich | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 11/2 | Fall Dance Team | Greenwich | Home - Tiger Hollow Stadium [Directions] | 7:00 p.m. | ||
| Fri., 11/2 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-9:00pm | ||
| Sat., 11/3 | JV Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | 8 am | |
| Sat., 11/3 | FR Football | Greenwich | Away - GHS Field 7 [Directions] | 10:00 a.m. | 8 am | |
| Sat., 11/3 | V Boys Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Sat., 11/3 | V Girls Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | team qualified for tournament | |
| Sat., 11/3 | V Girls Volleyball | FCIAC Tournament Finals at Fairfield Ludlowe | Away | 3:00 p.m. | did not qualify | |
| Sat., 11/3 | Miscellaneous Events | RYFH Tournament | Home - Tiger Hollow Stadium [Directions] | 8:30 a.m.-12:30pm | ||
| Sat., 11/3 | Miscellaneous Events | RYFH Tournament | Home - Tiger Hollow Turf Field II [Directions] | 8:30 a.m.-12:30pm | ||
| Sat., 11/3 | Miscellaneous Events | RYF | Home [Directions] | 1:00 p.m.-2pm | ||
| Sat., 11/3 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 5:00 p.m.-8pm | ||
| Sat., 11/3 | School Holidays and Closings | SAT Test | ||||
| Sun., 11/4 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 11/4 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 12:00 p.m.-6pm | ||
| Mon., 11/5 | V Field Hockey | Fairfield Ludlowe | Home - Tiger Hollow Turf Field II [Directions] | W 3-0 | ||
| Mon., 11/5 | V Girls Soccer | Manchester | Home - Tiger Hollow Stadium [Directions] | W 4-0 | ||
| Mon., 11/5 | V Girls Volleyball | Wilbur Cross | Home - RHS Main Gym [Directions] | W 3-2 | ||
| Mon., 11/5 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 11/5 | Unified Sports Soccer | Soccer Tournament at Staples HS | Away [Directions] | 3:00 p.m. | 2 pm | pick up at Community Entrance |
| Tue., 11/6 | V Boys Soccer | CIAC Tourney 1st Round | Away - Higher Seed | TBA | ||
| Tue., 11/6 | Miscellaneous Events | RBA Clinic | Home - RHS Main and Aux Gyms [Directions] | 12:00 p.m.-3:00pm | ||
| Tue., 11/6 | Miscellaneous Events | RBA Clinic | Home - RHS Main and Aux Gyms [Directions] | 12:00 p.m.-3pm | ||
| Tue., 11/6 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15 p.m. | ||
| Tue., 11/6 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Tue., 11/6 | School Holidays and Closings | No school for students - PD for staff | Election Day | |||
| Wed., 11/7 | V Field Hockey | Enfield | Away - Higher Seed [Directions] | L 3-2 | 1 pm | |
| Wed., 11/7 | V Girls Soccer | South Windsor | Home - Higher Seed [Directions] | W 4-0 | ||
| Wed., 11/7 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Wed., 11/7 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Thu., 11/8 | FR Football | Fairfield Warde | Home - Tiger Hollow II [Directions] | 4:00 p.m. | ||
| Thu., 11/8 | V Boys Soccer | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Thu., 11/8 | V Girls Volleyball | Cheshire | Away - Cheshire High - West Gym [Directions] | L 3-0 | 3:30 pm | |
| Thu., 11/8 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15p.m. | ||
| Thu., 11/8 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Thu., 11/8 | School Holidays and Closings | Winter Sports Kick Off Meeting for Parents and Students | ||||
| Fri., 11/9 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 29-0 | 4:15 pm | |
| Fri., 11/9 | V Sideline Cheerleading | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | 5:15 pm | |
| Fri., 11/9 | V Field Hockey | CIAC Tourney Quarterfinals (Possible Date) | Away - Higher Seed | TBA | ||
| Fri., 11/9 | V Girls Soccer | Darien | Home - Tiger Hollow Stadium [Directions] | W 1-0 | ||
| Fri., 11/9 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15p.m. | ||
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | JV Football | Fairfield Warde | Home - Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/10 | V Boys Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | JV Sideline Cheerleading | Fairfield Warde | Home - Tiger Hollow Turf Field II [Directions] | 10:30 a.m. | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | V Field Hockey | CIAC Tourney Quarterfinals (Possible Date) | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | 8 am | |
| Sat., 11/10 | V Girls Volleyball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | did not qualify | |
| Sat., 11/10 | Miscellaneous Events | RYF | Home - Tiger Hollow Turf Field II [Directions] | 11:30 a.m.-12:30pm | ||
| Sun., 11/11 | School Holidays and Closings | Veterans Day | ||||
| Mon., 11/12 | V Girls Soccer | Simsbury | Away - Municipal Stadium, Waterbury [Directions] | W 3-0 | 4 pm | |
| Mon., 11/12 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 11/12 | School Holidays and Closings | Veterans Day observed - School closed | ||||
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15p.m. | ||
| Tue., 11/13 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Wed., 11/14 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 6:00 p.m. | 3 pm | |
| Wed., 11/14 | V Girls Volleyball | CIAC Tourney Semifinals | Away - Site TBA | TBA | did not qualify | |
| Wed., 11/14 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 8:00 p.m.-9pm | ||
| Wed., 11/14 | Unified Sports Soccer | Joel Barlow (Scrim.) | Home - RHS Aux Gym [Directions] | Cancelled | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/15 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15p.m. | ||
| Thu., 11/15 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10:00pm | ||
| Fri., 11/16 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 5:00 p.m.-6pm | ||
| Fri., 11/16 | Miscellaneous Events | SCOR | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Fri., 11/16 | Miscellaneous Events | RYF | - Tiger Hollow Turf Field II | 6:00 p.m.-8:15p.m. | ||
| Sat., 11/17 | JV Football | Danbury | Home - Tiger Hollow II [Directions] | Cancelled | ||
| Sat., 11/17 | V Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | JV Sideline Cheerleading | Danbury | Home - Tiger Hollow Turf Field II [Directions] | Cancelled | ||
| Sat., 11/17 | V Field Hockey | CIAC Tourney Final | Away - Wethersfield [Directions] | TBA | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | 8:30 am | |
| Sat., 11/17 | V Girls Volleyball | CIAC Tourney Final | Away - East Haven [Directions] | TBA | did not qualify | |
| Sun., 11/18 | V Girls Soccer | Staples | Away - West Haven HS - Ken Strong Stadium [Directions] | W 1-0 | 12:00 pm | |
| Sun., 11/18 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Sun., 11/18 | Miscellaneous Events | SCOR | - Tiger Hollow Stadium | 9:00 a.m.-3pm | ||
| Sun., 11/18 | Miscellaneous Events | Youth Rugby Clinic | Home - Tiger Hollow Turf Field II [Directions] | 12:00 p.m.-3pm | ||
| Mon., 11/19 | FR Football | Danbury | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 11/19 | Miscellaneous Events | RYFH | - Tiger Hollow Turf Field II | 6:00 p.m.-7:30pm | ||
| Mon., 11/19 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 8:00 p.m.-9pm | ||
| Tue., 11/20 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 11/21 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 19-12 | 3:45 pm | 2 XL buses/ drop off pick up at 7:30 pm |
| Wed., 11/21 | V Sideline Cheerleading | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | 3:30 pm | drop off, return pick up at 7 pm |
| Wed., 11/21 | School Holidays and Closings | Early dismissal - Thanksgiving recess | ||||
| Thu., 11/22 | School Holidays and Closings | Thanksgiving Day - School closed | ||||
| Fri., 11/23 | School Holidays and Closings | Thanksgiving recess | ||||
| Sun., 11/25 | Miscellaneous Events | RAMS | Home - Tiger Hollow Turf Field II [Directions] | 8:00 a.m.-10am | ||
| Tue., 11/27 | V Football | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 12/1 | V Girls Basketball | Lady Hatters Jamboree @ Danbury | Away | 12:00 p.m. | 11:00 am | drop off, pick up at 5 pm |
| Sat., 12/1 | V Girls Ice Hockey | High School Girls Jamboree at the Rinks at Shelton | Away | TBA | 3:45 pm | team pick up/drop off at Winter Garden Ice Arena |
| Sat., 12/1 | School Holidays and Closings | SAT Test | ||||
| Sun., 12/2 | V Football | CIAC Tourney Semifinals | Away - Higher Seed | TBA | ||
| Mon., 12/3 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | W 2-0 | 3:30 pm | team pick up/drop off at Winter Garden Ice Arena |
| Mon., 12/3 | School Holidays and Closings | First day of Chanukah | ||||
| Wed., 12/5 | V Boys Basketball | Newtown (Scrim.) | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/6 | V Girls Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 5:15 p.m. | 4 pm | |
| Sat., 12/8 | V Boys Basketball | Preseason jamboree @TBA | Away | 6:00 p.m. | 3:00 pm | at Windsor HS |
| Sat., 12/8 | V Football | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 12/8 | V Boys Ice Hockey | St. Johns Prep (MA) (Scrim.) | Home - Winter Garden Ice Arena [Directions] | 11:30 a.m. | ||
| Sat., 12/8 | V Girls Basketball | Mercy (Scrim.) | Away - Mercy [Directions] | 3:30 p.m. | 1 pm | |
| Sat., 12/8 | School Holidays and Closings | ACT Test | ||||
| Mon., 12/10 | School Holidays and Closings | Last day of Chanukah | ||||
| Tue., 12/11 | V Boys Basketball | WCA (Scrim.) | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/12 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | W 5-2 | 3 pm | pick up/ drop off at Winter Gardetn |
| Wed., 12/12 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice, Bridgeport, CT [Directions] | 4:00 p.m. | 2 pm | at Wonderland of Ice |
| Wed., 12/12 | V Wrestling | Fairfield Warde | Home - RHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/12 | V Girls Basketball | Westhill | Home - RHS Main Gym [Directions] | W 60-33 | ||
| Wed., 12/12 | JV Girls Basketball | Westhill | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/12 | FR Girls Basketball | Pomperaug | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Winter Garden Ice Arena [Directions] | T 2-2(OT) | ||
| Thu., 12/13 | School Holidays and Closings | Early dismissal - PD for staff | ||||
| Fri., 12/14 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | at Dorothy Hamill Rink | |
| Fri., 12/14 | V Competitive Cheerleading | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 12/14 | JV Competitive Cheerleading | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Fairfield Warde | Home - RHS Main Gym [Directions] | W 47-46 | ||
| Fri., 12/14 | JV Girls Basketball | Fairfield Warde | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Girls Basketball | Fairfield Warde | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | W 4-1 | 4:15 pm | Conf 45333 |
| Sat., 12/15 | V Boys Indoor Track | FCIAC Developmental # 1 at Staples | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 12/15 | V Boys Indoor Track | Coaches Hall of Fame Invitational | Away | TBA | at NY Armory | |
| Sat., 12/15 | V Wrestling | Battle at Wethersfield | Away | TBA | 6:30 am | |
| Sat., 12/15 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-8 | 6:30 pm | team pick up/drop off at Winter Garden Ice Arena |
| Sat., 12/15 | V Girls Indoor Track | FCIAC Developmental # 1 at Staples | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 12/15 | V Girls Indoor Track | Coaches Hall of Fame Invitational | Away | TBA | at NY Armory | |
| Mon., 12/17 | V Boys Basketball | Byram Hills (NY) | Home - RHS Main Gym [Directions] | W 51-50 | ||
| Mon., 12/17 | JV Boys Basketball | Byram Hills (NY) | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/17 | FR Boys Basketball | Bethel | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Boys Basketball | Trinity Catholic | Home - RHS Main Gym [Directions] | W 70-57 | ||
| Wed., 12/19 | JV Boys Basketball | Trinity Catholic | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Boys Basketball | Trinity Catholic | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Winter Garden Ice Arena [Directions] | W 7-1 | ||
| Wed., 12/19 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:30 pm | |
| Wed., 12/19 | V Wrestling | Wilton | Home - RHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/19 | V Competitive Cheerleading | Trinity Catholic | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/19 | JV Competitive Cheerleading | Trinity Catholic | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | L 55-33 | 2:30 pm | 1 bus V/JV girls basketball |
| Wed., 12/19 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30 pm | 1 bus V/JV girls basketball |
| Wed., 12/19 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Winter Garden Ice Arena [Directions] | W 6-1 | ||
| Thu., 12/20 | JV Boys Ice Hockey | Darien | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Stamford | Home - RHS Main Gym [Directions] | W 71-46 | ||
| Fri., 12/21 | JV Boys Basketball | Stamford | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Stamford | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | V Boys Ice Hockey | LaSalle Academy (RI) | Away | W 5-3 | 12:45 p.m. | conf 45334 |
| Fri., 12/21 | V Boys Indoor Track | Jim Mitchell Invitational | Away | 5:00 p.m. | 2:30 pm | drop off only |
| Fri., 12/21 | V Boys Swimming and Diving | Staples | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | W 40-33 | 3 pm | 1 bus V/JV girls basketball |
| Fri., 12/21 | JV Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | 3 pm | 1 bus V/JV girls basketball |
| Fri., 12/21 | FR Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 12/21 | V Girls Ice Hockey | New Canaan | Home - Winter Garden Ice Arena [Directions] | L 0-9 | ||
| Fri., 12/21 | V Girls Indoor Track | Jim Mitchell Invitational | Away | 5:00 p.m. | 2:15 pm | at NYC Armory |
| Fri., 12/21 | School Holidays and Closings | Early dismissal - winter recess | ||||
| Sat., 12/22 | V Wrestling | Darien, Stamford, Norwalk, John Jay (NY) | Home - RHS Main and Aux Gyms [Directions] | 10:00 a.m. | ||
| Mon., 12/24 | JV Boys Ice Hockey | Carrano Cup Tournament at the Rinks at Shelton | Away | TBA | ||
| Mon., 12/24 | School Holidays and Closings | Christmas Eve | School closed | |||
| Tue., 12/25 | School Holidays and Closings | Christmas Day | School closed | |||
| Wed., 12/26 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | W 60-55 | 4:00 pm | at Bunnell HS |
| Wed., 12/26 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:00 p.m. | 1 pm | |
| Wed., 12/26 | V Boys Indoor Track | North Shore Invitational at NYC Armory | Away | 9:00 a.m. | 6:15 am | 2 buses B/G Track buses to stay with team |
| Wed., 12/26 | V Girls Ice Hockey | Avon | Home - Winter Garden Ice Arena [Directions] | L 3-4 | ||
| Wed., 12/26 | V Girls Indoor Track | North Shore Invitational at NYC Armory | Away | 9:00 a.m. | 6:15 am | at NY Armory |
| Wed., 12/26 | School Holidays and Closings | Winter recess | ||||
| Thu., 12/27 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Winter Garden Ice Arena [Directions] | W 6-1 | ||
| Thu., 12/27 | V Wrestling | Friar Bash - St. Anthony's (NY) | Away | TBA | 5:15 am | |
| Thu., 12/27 | School Holidays and Closings | Winter recess | ||||
| Fri., 12/28 | V Boys Basketball | Bassick | Away [Directions] | L 46-60 | 3:45 pm | |
| Fri., 12/28 | JV Boys Basketball | Hardwood Holiday Classic @ Bunnell | Away | TBA | TBA | |
| Fri., 12/28 | JV Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 7:45 p.m. | at Shelton Rinks | |
| Fri., 12/28 | V Wrestling | Friar Bash - St. Anthony's (NY) | Away | TBA | ||
| Fri., 12/28 | V Girls Basketball | Pomperaug | Away [Directions] | L 39-42 | 9:30 am | Newtown Holiday Tournament at Newtown HS |
| Fri., 12/28 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Winter Garden Ice Arena [Directions] | W 8-2 | ||
| Fri., 12/28 | School Holidays and Closings | Winter recess | ||||
| Sat., 12/29 | JV Boys Ice Hockey | Carrano Cup Championship at The Rinks at Shelton | Away | 4:45 p.m. | ||
| Sat., 12/29 | V Girls Basketball | Mansfield (MA) | Away [Directions] | L 40-32 | 10:30 am | Newtown Holiday Tournament at Newtown HS |
| Mon., 12/31 | School Holidays and Closings | New Years Eve - Winter recess | ||||
| Tue., 1/1 | School Holidays and Closings | New Years Day | School closed | |||
| Thu., 1/3 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | L 49-50 | 3 pm | 1 bus V/JV boys basketball |
| Thu., 1/3 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | 3 pm | 1 bus V/JV boys basketball |
| Thu., 1/3 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 1/3 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 5:00 p.m. | 2:45 pm | |
| Thu., 1/3 | V Girls Basketball | Trumbull | Home - RHS Main Gym [Directions] | L 44-58 | ||
| Thu., 1/3 | JV Girls Basketball | Trumbull | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | FR Girls Basketball | Trumbull | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/4 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 4:50 p.m. | 2:20 pm | from RHS |
| Fri., 1/4 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | W 6-1 | 10:45 am | pick up/drop off at Winter Garden |
| Sat., 1/5 | V Boys Indoor Track | FCIAC Developmental # 2 at Wilton | Away [Directions] | 9:30 a.m. | 8 am | |
| Sat., 1/5 | V Wrestling | Amity | Away [Directions] | TBA | 7:00 am | |
| Sat., 1/5 | V Girls Ice Hockey | Greenwich | Home - Winter Garden Ice Arena [Directions] | W 2-1 | ||
| Sat., 1/5 | V Girls Indoor Track | Ocean Breeze Freedom Games | Away | Cancelled | TBA | |
| Sat., 1/5 | V Girls Indoor Track | FCIAC Developmental # 2 at Wilton | Away [Directions] | 9:30 a.m. | 8 am | |
| Mon., 1/7 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 55-62 | 3:45 pm | 1 bus V/JV boys basketball |
| Mon., 1/7 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | 3:45 pm | 1 bus V/JV boys basketball |
| Mon., 1/7 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 1/7 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | 8:40 p.m. | no bus | |
| Mon., 1/7 | JV Wrestling | Danbury, Wilton, New Milford | Home - RHS Aux Gym [Directions] | 3:00 p.m. | ||
| Mon., 1/7 | V Competitive Cheerleading | Danbury | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/7 | JV Competitive Cheerleading | Danbury | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | V Girls Basketball | Danbury | Home - RHS Main Gym [Directions] | L 36-44 | ||
| Mon., 1/7 | JV Girls Basketball | Danbury | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Girls Basketball | Danbury | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | JV Boys Ice Hockey | Greenwich | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 1/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 13-2 | 7 pm | team pick up/drop off at Winter Garden Ice Arena |
| Wed., 1/9 | V Boys Ice Hockey | Staples | Home - Winter Garden Ice Arena [Directions] | W 9-0 | ||
| Wed., 1/9 | V Wrestling | Staples, Danbury | Away [Directions] | 6:00 p.m. | 5:30 pm | |
| Wed., 1/9 | V Co-ed Alpine Skiing | Ski Race at Mt. Southington | Away | 4:00 p.m. | 2 pm | Conf 45839 |
| Wed., 1/9 | FR Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:30 pm | |
| Thu., 1/10 | V Boys Basketball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | W 61-53 | ||
| Thu., 1/10 | JV Boys Basketball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/10 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 53-57(OT) | 3:30 pm | 1 bus V/JV Girls Basketball |
| Thu., 1/10 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 3:30 pm | 1 bus V/JV Girls Basketball |
| Thu., 1/10 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 1/10 | School Holidays and Closings | Early dismissal - PD for staff | ||||
| Fri., 1/11 | V Boys Ice Hockey | Darien | Home - Winter Garden Ice Arena [Directions] | W 3-2(OT) | ||
| Fri., 1/11 | V Boys Indoor Track | Yale Classic | Away | 3:00 p.m. | ||
| Fri., 1/11 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | 1:45 pm | 1:30 early dismissal |
| Fri., 1/11 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | L 2-5 | 6:15 pm | team pick up/drop off at Winter Garden Ice Arena |
| Fri., 1/11 | V Girls Indoor Track | Yale Classic | Away | 3:00 p.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | W 2-0 | 3 pm | pick up/drop off at Winter Garden |
| Sat., 1/12 | V Boys Indoor Track | FCIAC Developmental # 3 at Staples | Away | 10:00 a.m. | 8:30 am | |
| Sat., 1/12 | V Boys Indoor Track | Yale Classic | Away | 7:00 a.m. | ||
| Sat., 1/12 | V Wrestling | Greater Hartford Wrestling Tournament | Away | 9:15 a.m. | 6:15 am | weigh ins at 7:30 am |
| Sat., 1/12 | V Competitive Cheerleading | Hatter Fest 2019 at DHS | Away [Directions] | TBA | 8 am | drop off/ pick up at 1 pm |
| Sat., 1/12 | Winter Dance Team | Dancin in the Woods Tournament | Away | TBA | 12:40 pm | at Woodland Regional High School, Beacon Falls, CT |
| Sat., 1/12 | V Girls Indoor Track | FCIAC Developmental # 3 at Staples | Away | 10:00 a.m. | 8:30 am | |
| Sat., 1/12 | V Girls Indoor Track | Yale Classic | Away | 7:00 a.m. | ||
| Mon., 1/14 | V Boys Basketball | Greenwich | Home - RHS Main Gym [Directions] | W 49-36 | ||
| Mon., 1/14 | JV Boys Basketball | Greenwich | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Greenwich | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | V Competitive Cheerleading | Greenwich | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/14 | JV Competitive Cheerleading | Greenwich | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | V Girls Basketball | Greenwich | Away - Scofield Magnet MS [Directions] | W 49-35 | 3:00 pm | |
| Mon., 1/14 | V Girls Ice Hockey | Northwest Catholic | Home - Winter Garden Ice Arena [Directions] | L 1-2 | ||
| Tue., 1/15 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | W 6-1 | 3:40 pm | pick up/drop off at Winter Garden |
| Wed., 1/16 | V Boys Swimming and Diving | Trumbull | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Wed., 1/16 | V Wrestling | Greenwich, Brien McMahon | Away - GHS Gymnasium [Directions] | 5:00 p.m. | 2:45 pm | |
| Wed., 1/16 | V Co-ed Alpine Skiing | Ski Race at Mt. Southington | Away | 4:00 p.m. | 2 pm | Conf 45840 |
| Wed., 1/16 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Winter Garden Ice Arena [Directions] | W 5-0 | ||
| Thu., 1/17 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 58-60 | 3:15 pm | 1 bus V/JV boys basketball |
| Thu., 1/17 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV boys basketball |
| Thu., 1/17 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 1/17 | V Girls Basketball | Brien McMahon | Home - RHS Main Gym [Directions] | W 57-25 | ||
| Thu., 1/17 | JV Girls Basketball | Brien McMahon | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | L 1-3 | 2:15 pm | team pick up/drop off at Winter Garden Ice Arena |
| Sat., 1/19 | V Boys Indoor Track | New Balance Games | Away | 9:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | FCIAC Developmental # 4 at Wilton | Away | 9:30 a.m. | 8 am | |
| Sat., 1/19 | V Wrestling | Brunswick Tournament | Away | TBA | 6:45 am | at Brunswick King Street Campus |
| Sat., 1/19 | V Competitive Cheerleading | Ludlowe Cheer Open at Fairfield Ludlowe HS | Away [Directions] | TBA | 7:30 am | Drop off/pick up at 1 pm |
| Sat., 1/19 | JV Girls Basketball | Greenwich | Away - Western MS [Directions] | 10:30 a.m. | 7:30 am | 1 bus JV/FR girls basketball |
| Sat., 1/19 | FR Girls Basketball | Greenwich | Away - Western MS [Directions] | 9:00 a.m. | 7:30 am | 1 bus JV/FR girls basketball |
| Sat., 1/19 | V Girls Indoor Track | New Balance Games | Away | 9:00 a.m. | ||
| Sat., 1/19 | V Girls Indoor Track | FCIAC Developmental # 4 at Wilton | Away [Directions] | 9:30 a.m. | 8 am | |
| Mon., 1/21 | JV Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | 3:15 p.m. | ||
| Mon., 1/21 | V Boys Indoor Track | Frosh/Soph meet at Hillhouse HS | Away | Cancelled | ||
| Mon., 1/21 | V Girls Indoor Track | Frosh/Soph meet at Hillhouse | Away [Directions] | 12:00 p.m. | First Student | |
| Mon., 1/21 | School Holidays and Closings | Martin Luther King Day | School closed | |||
| Tue., 1/22 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 1/22 | V Competitive Cheerleading | Bridgeport Central | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/22 | JV Competitive Cheerleading | Bridgeport Central | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | V Girls Basketball | Bridgeport Central | Home - RHS Main Gym [Directions] | W 78-20 | ||
| Tue., 1/22 | JV Girls Basketball | Bridgeport Central | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 81-63 | 3:00 pm | 1 bus V/JV boys basketball |
| Wed., 1/23 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | 3:00 pm | 1 bus V/JV boys basketball |
| Wed., 1/23 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 1/23 | V Girls Basketball | Capital Prep | Home - RHS Main Gym [Directions] | L 44-58 | ||
| Wed., 1/23 | JV Girls Basketball | Capital Prep | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/23 | FR Girls Basketball | New Fairfield | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Girls Ice Hockey | Darien | Home - Winter Garden Ice Arena [Directions] | L 1-6 | ||
| Fri., 1/25 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | W 67-51 | 3:15 pm | |
| Fri., 1/25 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV boys basketball |
| Fri., 1/25 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 1/25 | V Boys Ice Hockey | Greenwich | Home - Winter Garden Ice Arena [Directions] | W 5-2 | ||
| Fri., 1/25 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | 1:30 pm | 1:15 early dismissal |
| Fri., 1/25 | V Competitive Cheerleading | Darien | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/25 | JV Competitive Cheerleading | Darien | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Darien | Home - RHS Main Gym [Directions] | W 52-27 | Pink Night & Youth Night | |
| Fri., 1/25 | JV Girls Basketball | Darien | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Girls Basketball | Darien | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/26 | JV Boys Ice Hockey | Delbarton (NJ) | Away | 4:45 p.m. | 1 pm | at Aspen Ice, Randolph, NJ/pick up drop off from RHS |
| Sat., 1/26 | V Boys Indoor Track | FCIAC Eastern Divisional at Wilton | Away | 9:30 a.m. | 8 am | |
| Sat., 1/26 | V Wrestling | Ridgefield Challenge | Home - RHS Main and Aux Gyms [Directions] | 9:00 a.m. | ||
| Sat., 1/26 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | W 6-1 | 12:30 pm | team pick up/drop off at Winter Garden Ice Arena |
| Sat., 1/26 | V Girls Indoor Track | FCIAC Eastern Divisional at Wilton | Away | 9:30 a.m. | 8 am | |
| Sun., 1/27 | Miscellaneous Events | Ridgefield Youth Wrestling Tournament | Home - RHS Main and Aux Gyms [Directions] | 6:00 a.m.-9 p.m. | ||
| Mon., 1/28 | JV Boys Ice Hockey | Brunswick School | Away | 5:30 p.m. | 4 pm | game at Hartong Rink, 1252 King St, Greenwich |
| Mon., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 1-4 | 4:15 pm | team pick up/drop off at Winter Garden Ice Arena |
| Wed., 1/30 | Miscellaneous Events | RHS VPA | Home - RHS Main Gym [Directions] | 2:30 p.m.-3:30pm | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championship at Floyd Little Athletic Center | Away | 5:30 p.m. | 2:30 pm | |
| Thu., 1/31 | V Wrestling | Westhill | Away - Westhill - New Gymnasium [Directions] | 5:00 p.m. | 3 pm | |
| Thu., 1/31 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 2-8 | 5:45 pm | at Dorothy Hamill rink |
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championship at Floyd Little Atheletic Center | Away | 5:30 p.m. | 2:30 pm | |
| Fri., 2/1 | V Boys Basketball | Wilton | Home - RHS Main Gym [Directions] | W 62-44 | ||
| Fri., 2/1 | JV Boys Basketball | Wilton | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Wilton | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/1 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 5-1 | 2 pm | Charter 52421 |
| Fri., 2/1 | JV Boys Ice Hockey | Darien | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:15 pm | 1 pm early dismissal |
| Fri., 2/1 | V Competitive Cheerleading | Wilton | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | JV Competitive Cheerleading | Wilton | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Career Magnet | Away - Career HS [Directions] | W 53-40 | 3 pm | 1 bus V/JV Girls Basketball |
| Fri., 2/1 | JV Girls Basketball | Career Magnet | Away - Career HS [Directions] | 5:15 p.m. | 3 pm | 1 bus V/JV Girls Basketball |
| Fri., 2/1 | Winter Dance Team | Wilton | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/2 | V Boys Basketball | John Jay (NY) | Home - RHS Main Gym [Directions] | W 60-56 | ||
| Sat., 2/2 | JV Boys Basketball | John Jay (NY) | Home - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/2 | FR Boys Basketball | John Jay (NY) | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/2 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | W 8-0 | 5 pm | conf 45337 |
| Sat., 2/2 | V Wrestling | Johnathan Law Tournament | Away | TBA | 6:30 am | |
| Sat., 2/2 | V Competitive Cheerleading | FCIAC Tournament at Wilton HS | Away | 11:00 a.m. | 8:15 am | drop off, pick up at 1:30 pm |
| Sat., 2/2 | Miscellaneous Events | Rebels baseball/softball | Home - RHS Aux Gym [Directions] | 4:00 p.m.-6pm | ||
| Mon., 2/4 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | W 7-0 | 2:20 pm | early dismissal at 2 pm |
| Mon., 2/4 | V Boys Swimming and Diving | Wilton | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Mon., 2/4 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | L 1-5 | 5 pm | team pick up/drop off at Winter Garden Ice Arena |
| Tue., 2/5 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 60-57 | 3:15 pm | 1 bus V/JV boys basketball |
| Tue., 2/5 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV boys basketball |
| Tue., 2/5 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 2/5 | JV Boys Ice Hockey | New Canaan | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 2/5 | V Wrestling | Staples | Home - RHS Aux Gym [Directions] | 6:30 p.m. | ||
| Tue., 2/5 | V Competitive Cheerleading | Staples | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/5 | JV Competitive Cheerleading | Staples | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Staples | Home - RHS Main Gym [Directions] | L 45-59 | ||
| Tue., 2/5 | JV Girls Basketball | Staples | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | Staples | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Winter Garden Ice Arena [Directions] | W 9-2 | ||
| Wed., 2/6 | V Co-ed Alpine Skiing | Ski Race at Mt. Southington | Away | 4:00 p.m. | 2 pm | Conf 45843 |
| Wed., 2/6 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 44-26 | 4 pm | 1 bus V/JV Girls Basketball |
| Wed., 2/6 | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | 4 pm | 1 bus V/JV Girls Basketball |
| Wed., 2/6 | FR Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:45 p.m. | 2:30 pm | |
| Wed., 2/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Winter Garden Ice Arena [Directions] | W 7-2 | ||
| Thu., 2/7 | V Boys Swimming and Diving | Greenwich | Home - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | St. Joseph | Home - RHS Main Gym [Directions] | W 88-50 | ||
| Fri., 2/8 | JV Boys Basketball | St. Joseph | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | St. Joseph | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Winter Garden Ice Arena [Directions] | W 8-2 | ||
| Fri., 2/8 | V Wrestling | FCIAC Championships - Day 1 @ New Canaan | Away | 4:30 p.m. | 2:15 pm | drop off, bus should return for 8 pm pick up |
| Fri., 2/8 | V Competitive Cheerleading | St. Joseph | Home - RHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/8 | JV Competitive Cheerleading | St. Joseph | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | W 47-38 | 3:15 pm | 1 bus V/JV Girls Basketball |
| Fri., 2/8 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV Girls Basketball |
| Fri., 2/8 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Sat., 2/9 | V Boys Ice Hockey | Simsbury | Away - ISCC [Directions] | W 5-3 | 3 pm | conf 45338 |
| Sat., 2/9 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | 2:30 pm | |
| Sat., 2/9 | V Wrestling | FCIAC Championships - Day 2 @ New Canaan | Away | 10:00 a.m. | ||
| Sat., 2/9 | V Competitive Cheerleading | Watertown HS Cheerfest | Away [Directions] | TBA | 7:30 am | drop off - pick up at 2:45 pm |
| Sat., 2/9 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | 2:30 pm | |
| Sat., 2/9 | School Holidays and Closings | ACT Test | ||||
| Mon., 2/11 | V Boys Basketball | New Canaan | Home - RHS Main Gym [Directions] | L 53-60 | ||
| Mon., 2/11 | JV Boys Basketball | New Canaan | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | New Canaan | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 38-16 | 3:30 pm | 1 bus V/JV Girls Basketball |
| Mon., 2/11 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | 3:30 pm | 1 bus V/JV Girls Basketball |
| Mon., 2/11 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - The Rinks at Shelton - upper [Directions] | W 8-0 | 4:45 pm | team pick up/drop off at Winter Garden Ice Arena |
| Wed., 2/13 | V Boys Ice Hockey | Fairfield Prep | Home - Winter Garden Ice Arena [Directions] | W 2-1 | ||
| Wed., 2/13 | V Boys Swimming and Diving | Danbury | Home - Pool at Barlow Mountain School [Directions] | 5:00 p.m. | ||
| Wed., 2/13 | V Co-ed Alpine Skiing | Race at Mt. Southington | Away | 4:00 p.m. | 2 pm | Conf 46068 |
| Wed., 2/13 | V Girls Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | L 34-48 | 3:45 pm | 1 bus V/JV Girls Basketball |
| Wed., 2/13 | JV Girls Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | 3:45 pm | 1 bus V/JV Girls Basketball |
| Wed., 2/13 | FR Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:45 p.m. | 2:30 pm | |
| Thu., 2/14 | V Boys Basketball | Norwalk | Home - RHS Main Gym [Directions] | W 82-50 | ||
| Thu., 2/14 | JV Boys Basketball | Norwalk | Home - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/14 | FR Boys Basketball | Norwalk | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/14 | V Competitive Cheerleading | Norwalk | Home - RHS Main Gym [Directions] | 7:00 p.m. | Senior Night | |
| Thu., 2/14 | JV Competitive Cheerleading | Norwalk | Home - RHS Main Gym [Directions] | 7:00 p.m. | Senior Night | |
| Thu., 2/14 | School Holidays and Closings | Early Dismissal - PD for staff | ||||
| Fri., 2/15 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 10-3 | ||
| Fri., 2/15 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:45 p.m. | 1 pm | |
| Fri., 2/15 | School Holidays and Closings | February recess | ||||
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | ||
| Sat., 2/16 | V Girls Basketball | Trumbull | Away [Directions] | W 41-40 | 11:30 am | at Fairfield Ludlowe |
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 9:30 am | |
| Mon., 2/18 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 77-52 | 3:15 pm | 1 bus V/JV boys basketball |
| Mon., 2/18 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV boys basketball |
| Mon., 2/18 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 2/18 | V Boys Ice Hockey | Westhill/Stamford | Home - Winter Garden Ice Arena [Directions] | W 7-1 | ||
| Mon., 2/18 | JV Wrestling | Presidents' Day Tournament @ Pomperaug | Away | 9:00 a.m. | 7 am | team did not cancel with athletic dept. bus showed up - paid 1 hour cancellation charge |
| Mon., 2/18 | School Holidays and Closings | February Recess | ||||
| Tue., 2/19 | JV Boys Ice Hockey | Xavier | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 2/19 | V Girls Basketball | Trinity Catholic | Away [Directions] | L 50-35 | 4:45 pm | FCIAC Tournament Semi Finals at Trumbull HS |
| Tue., 2/19 | School Holidays and Closings | February recess - PD for staff | ||||
| Wed., 2/20 | V Girls Ice Hockey | FCIAC Tournament Semi Finals at Darien Ice Rink | Away | TBA | did not qualify | |
| Thu., 2/21 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 53-60 | 3:15 pm | 1 bus V/JV boys basketball |
| Thu., 2/21 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | 3:15 pm | 1 bus V/JV boys basketball |
| Thu., 2/21 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 2/21 | JV Boys Ice Hockey | Brunswick School | Away | 6:00 p.m. | 4:00 pm | |
| Thu., 2/21 | V Girls Basketball | FCIAC Tournament Finals at Trumbull HS | Away | 7:00 p.m. | ||
| Fri., 2/22 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:30 p.m. | at Darien Ice Rink | |
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | 10:45 am | pick up at RHS, drop off only at Floyd Little |
| Sat., 2/23 | V Boys Basketball | New Canaan | Away [Directions] | W 51-44 | 2:45 pm | FCIAC Qtr Finals at Fairfield Warde -drop off only |
| Sat., 2/23 | V Boys Ice Hockey | FCIAC Tournament Playdowns | Away | TBA | Bye in playdowns | |
| Sat., 2/23 | JV Boys Ice Hockey | Darien | Home - Danbury Ice Arena [Directions] | 4:50 p.m. | JV Championship game | |
| Sat., 2/23 | JV Boys Swimming and Diving | FCIAC JV Tournament at Greenwich HS | Away | Cancelled | ||
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sat., 2/23 | V Competitive Cheerleading | Hawks Nest Cheer Competition at Woodland Regional HS, Beacon Falls, CT | Away | 10:00 a.m. | 7 am | at Woodland Regional HS in Beacon Falls, CT |
| Sat., 2/23 | Winter Dance Team | CAS Dance Team Championship at Hamden HS | Away [Directions] | TBA | 7:50 am | |
| Sat., 2/23 | V Girls Ice Hockey | FCIAC Tournament Finals at Darien Ice Rink | Away | 4:00 p.m. | did not qualify | |
| Sun., 2/24 | JV Boys Ice Hockey | Immaculate | Away - Danbury Arena [Directions] | 2:20 p.m. | ||
| Mon., 2/25 | Miscellaneous Events | Unified Basketball Tournament | Home - RHS Main and Aux Gyms [Directions] | 2:30 p.m.-5:15pm | ||
| Tue., 2/26 | V Boys Basketball | Trumbull | Away [Directions] | W 73-66 | 5 pm | FCIAC Semi Finals at Wilton HS |
| Tue., 2/26 | JV Boys Ice Hockey | St. Joseph | Home - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Tournament Trials at Greenwich | Away [Directions] | 5:30 p.m. | 2:45 pm | |
| Tue., 2/26 | V Girls Basketball | Wilbur Cross | Away - Higher Seed [Directions] | L 60-39 | 4:30 pm | |
| Wed., 2/27 | V Boys Ice Hockey | Westhill/Stamford | Home - Winter Garden Ice Arena [Directions] | W 8-1 | FCIAC Tournament Semi Finals | |
| Wed., 2/27 | V Boys Swimming and Diving | FCIAC Tournament Diving Finals at Westhill | Away [Directions] | 5:00 p.m. | ||
| Thu., 2/28 | V Boys Basketball | Danbury | Away [Directions] | W 52-49 | 4:45 pm | FCIAC Tournament Finals at Wilton HS |
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Finals at Greenwich | Away [Directions] | 6:30 p.m. | 4 pm | |
| Thu., 2/28 | V Co-ed Alpine Skiing | Ski Race at Mt. Southington | Away | 4:00 p.m. | 2 pm | Conf 45842- 1/31/19 reschedule |
| Thu., 2/28 | V Competitive Cheerleading | Danbury | Away [Directions] | 7:00 p.m. | 5:45 pm | FCIAC Boys Basketball Finals at Wilton HS |
| Fri., 3/1 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Sat., 3/2 | V Boys Ice Hockey | Greenwich | Away [Directions] | W 8-1 | 3:30 pm | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 3/3 | V Competitive Cheerleading | CIAC Cheer Championships at Floyd Little Athletic Center | Away | 9:00 a.m. | 7 am | |
| Mon., 3/4 | V Boys Basketball | CIAC Tourney 1st Round | Away - Higher Seed | TBA | bye in first round of tourney | |
| Tue., 3/5 | V Boys Ice Hockey | CIAC Tourney 1st Round | Away - Higher Seed | TBA | bye | |
| Tue., 3/5 | V Co-ed Alpine Skiing | Ski Championship at Mt Southington | Away | 2:00 p.m. | 11 am | Conf 47219 |
| Wed., 3/6 | V Boys Basketball | Immaculate | Away - Pomperaug HS [Directions] | L 71-67 | 4 pm | CIAC Tournament 2nd Round at Pomperaug HS |
| Wed., 3/6 | School Holidays and Closings | Spring Sports Kick Off Meeting for Parents and Students | ||||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 3/9 | V Boys Ice Hockey | Xavier | Away - Site TBA [Directions] | L 3-2 | 1:15 p.m. | at Bennett Rink, 1 Circle St, West Haven, CT 06516 |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford HS [Directions] | 6:00 p.m. | 2:30 pm | |
| Sat., 3/9 | School Holidays and Closings | SAT Test | ||||
| Mon., 3/11 | V Boys Basketball | CIAC Tourney Quarterfinals | Away - Site TBA | TBA | did not qualify | |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 1:30 p.m. | 10:30 am | |
| Mon., 3/11 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Mon., 3/11 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 3/11 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Mon., 3/11 | Unified Sports Basketball | Unified Tournamnet at Fairfield Ludlowe | Away | 3:30 p.m. | 2:30 pm | 10 students plus 2 coaches |
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Tue., 3/12 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 3/12 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 3/13 | V Boys Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | did not qualify | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Tourney Semifinals | Away - Ingalls Rink [Directions] | TBA | ||
| Wed., 3/13 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 3/13 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | 4 pm | |
| Thu., 3/14 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 3/14 | School Holidays and Closings | Early dismissal - PD for staff | ||||
| Fri., 3/15 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 3/15 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 3/16 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | did not qualify | |
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sat., 3/16 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 3/17 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | did not qualify | |
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-6pm | ||
| Sun., 3/17 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Mon., 3/18 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 3/18 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 3/19 | V Boys Ice Hockey | CIAC Tourney Final | Away - Ingalls Rink [Directions] | 7:00 p.m. | ||
| Tue., 3/19 | Miscellaneous Events | RYL | Home - Tiger Hollow Stadium [Directions] | 6:00 p.m.-7pm | ||
| Tue., 3/19 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 3/20 | V Boys Volleyball | Preseason Jamboree | Home - RHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 3/20 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 3/20 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 3/21 | V Boys Lacrosse | @ John Jay - East Fishkill | Away | 4:30 p.m. | 3:00 pm | |
| Thu., 3/21 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Fri., 3/22 | V Girls Lacrosse | North Salem (NY) (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | JV Girls Lacrosse | North Salem (NY) (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Fri., 3/22 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 3/22 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 3/23 | V Boys Lacrosse | Preseason Jamboree @ New Fairfield | Away | 8:15 a.m. | 8:45 am | |
| Sat., 3/23 | V Girls Lacrosse | Preseason Jamboree | Home - Tiger Hollow Stadium [Directions] | 9:00 a.m.-12pm | ||
| Sat., 3/23 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 1:00 p.m.-6pm | ||
| Sat., 3/23 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 3:00 p.m.-7pm | ||
| Sun., 3/24 | V Boys Rugby | Keio Academy, Purchase, NY | Away | 11:00 a.m. | 10 am | |
| Sun., 3/24 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-6pm | ||
| Sun., 3/24 | Miscellaneous Events | RYL-Referee training | - Tiger Hollow Turf Field II | 12:30 p.m.-5:30pm | ||
| Mon., 3/25 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 3/25 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 3/26 | V Baseball | New Fairfield (Scrim.) | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Joel Barlow (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Tue., 3/26 | JV Girls Lacrosse | Joel Barlow (Scrim.) | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Tue., 3/26 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 3/27 | V Baseball | Bethel (Scrim.) | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 3:30 p.m. | ||
| Wed., 3/27 | V Girls Lacrosse | @ Sacred Heart Academy - Greenwich | Away | 4:30 p.m. | 2:30 pm | |
| Wed., 3/27 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 3/27 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 3/28 | V Softball | North Salem (NY) (Scrim.) | Home - Tiger Ridge Softball Field (RHS) [Directions] | 4:15 p.m. | ||
| Thu., 3/28 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 3/28 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 3/29 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 3/29 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 3/30 | V Baseball | New Milford | Away - New Milford HS [Directions] | W 6-0 | 10 am | |
| Sat., 3/30 | JV Baseball | New Milford | Away - New Milford HS [Directions] | L 3-7 | 10 am | |
| Sat., 3/30 | V Boys Rugby | Fairfield Prep | Away [Directions] | 3:00 p.m. | 1 pm | |
| Sat., 3/30 | V Boys Volleyball | Masuk | Home - RHS Main Gym [Directions] | L 1-3 | ||
| Sat., 3/30 | JV Boys Volleyball | Masuk | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 3/30 | V Softball | Staples | Away - Wakeman Field [Directions] | L 9-10 | 10:30 am | Non-league game |
| Sat., 3/30 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 3/31 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-6pm | ||
| Sun., 3/31 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 3/31 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 a.m.-10am | ||
| Mon., 4/1 | V Boys Outdoor Track | Fairfield Ludlowe | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Boys Tennis | Trinity Catholic | Home - RHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/1 | V Boys Volleyball | Staples | Home - RHS Main Gym [Directions] | L 1-3 | ||
| Mon., 4/1 | JV Boys Volleyball | Staples | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Girls Outdoor Track | Fairfield Ludlowe | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 5-10 | 2:30 pm | Non-league game |
| Mon., 4/1 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 4/1 | V Girls Tennis | Trinity Catholic | Away | W 6-1 [Detailed Results] | 2:30 pm | |
| Mon., 4/1 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 4/1 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 4/2 | V Baseball | Weston | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 5-1 | ||
| Tue., 4/2 | JV Baseball | Weston | Home - East Ridge MS [Directions] | W 6-6 | ||
| Tue., 4/2 | JV Boys Golf | New Fairfield (Scrim.) | Home - Silver Spring GC [Directions] | Cancelled | ||
| Tue., 4/2 | V Boys Lacrosse | Norwalk | Home - Tiger Hollow Stadium [Directions] | W 21-1 | ||
| Tue., 4/2 | JV Boys Lacrosse | Norwalk | Home - Tiger Hollow Turf Field II [Directions] | 5:00 p.m. | ||
| Tue., 4/2 | V Boys Rugby | Staples | Away [Directions] | 4:30 p.m. | 2:30 pm | |
| Tue., 4/2 | V Boys Tennis | Stamford | Home - RHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/2 | V Girls Lacrosse | Norwalk | Home - Tiger Hollow Stadium [Directions] | W 18-2 | ||
| Tue., 4/2 | JV Girls Lacrosse | Norwalk | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | W 5-2 [Detailed Results] | 2:30 pm | |
| Tue., 4/2 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 a.m.-10am | ||
| Tue., 4/2 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 4/3 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 3:00 pm | |
| Wed., 4/3 | JV Boys Volleyball | New Canaan | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 4/3 | JV Girls Tennis | Wilton | Home - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 4/3 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/4 | V Baseball | Newtown | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 8-6 | ||
| Thu., 4/4 | JV Baseball | Newtown | Home - East Ridge MS [Directions] | W 19-5 (5 inn) | ||
| Thu., 4/4 | FR Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | L 10-5 | 2:30 pm | |
| Thu., 4/4 | V Boys Golf | New Fairfield (Scrim.) | Home - Silver Spring GC [Directions] | 3:15 p.m. | ||
| Thu., 4/4 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | Cancelled | ||
| Thu., 4/4 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 5-2 | 2:30 pm | |
| Thu., 4/4 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 2-3 | 2:30 pm | Non-league game |
| Thu., 4/4 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:30 p.m. | 2:30 pm | |
| Thu., 4/4 | V Girls Tennis | Trumbull | Home - RHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Thu., 4/4 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-7pm | ||
| Thu., 4/4 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/4 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 p.m.-10pm | ||
| Fri., 4/5 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 6-14 | 4:30 pm | |
| Fri., 4/5 | JV Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 4/5 | V Boys Volleyball | Darien | Home - RHS Main Gym [Directions] | L 0-3 | ||
| Fri., 4/5 | JV Boys Volleyball | Darien | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 4/5 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 4/6 | V Baseball | Amity | Away - John Janenda Baseball Field @ Amity HS [Directions] | W 5-4 | TBA | |
| Sat., 4/6 | JV Baseball | Amity | Away - John Janenda Baseball Field @ Amity HS [Directions] | W 5-0 | 10 am | |
| Sat., 4/6 | FR Baseball | Amity | Home - Branchville Civic (Playground Field) [Directions] | W 8-2 | ||
| Sat., 4/6 | V Boys Rugby | Harvey School (NY) | Away | 11:00 a.m. | 10:15 am | JV game at Harvey School, 260 Jay Street, Katonah, NY |
| Sat., 4/6 | V Boys Volleyball | New Canaan | Home - RHS Main Gym [Directions] | L 2-3 | ||
| Sat., 4/6 | V Girls Lacrosse | John Jay (NY) | Away | L 10-11 | 5:30 pm | |
| Sat., 4/6 | JV Girls Lacrosse | John Jay (NY) | Away | 5:00 p.m. | 3:30 pm | |
| Sat., 4/6 | V Softball | Newtown | Away - Newtown HS Softball Field [Directions] | L 8-11 | 10:30 am | |
| Sat., 4/6 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 4/7 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-7pm | ||
| Sun., 4/7 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 4/7 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 9:00 a.m.-4pm | ||
| Sun., 4/7 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Mon., 4/8 | V Boys Golf | Norwalk | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | W. 146-189 | ||
| Mon., 4/8 | V Boys Lacrosse | Briarcliff (NY) | Home - Tiger Hollow Stadium [Directions] | W 13-6 | ||
| Mon., 4/8 | V Boys Tennis | Danbury | Home - RHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/8 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 0-3 | 2:30 pm | |
| Mon., 4/8 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Mon., 4/8 | V Girls Outdoor Track | Staples, Trumbull | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Danbury | Home - RHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 4/8 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 4/8 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 4/9 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | Cancelled | ||
| Tue., 4/9 | V Boys Outdoor Track | Trumbull, Staples | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 4/9 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | Ridgefield 192 Danbury 243 | 2 pm | |
| Tue., 4/9 | V Girls Lacrosse | Greenwich Academy | Home - Tiger Hollow Stadium [Directions] | L 16-5 | ||
| Tue., 4/9 | JV Girls Lacrosse | Greenwich Academy | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | FR Girls Lacrosse | Staples | Home - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Softball | Trinity Catholic | Away - Trinity Catholic's Smith Field | W 18-2 | 2:30 pm | |
| Tue., 4/9 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 4/9 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 4/10 | V Baseball | Stamford | Away - SHS Baseball Field [Directions] | W 6-3 | 2:30 pm | Pick up/drop off from RHS |
| Wed., 4/10 | JV Baseball | Stamford | Home - East Ridge MS [Directions] | W 12-0 (5 inn) | ||
| Wed., 4/10 | FR Baseball | Stamford | Away - Belltown Field [Directions] | W 12-0 | 2:30 pm | |
| Wed., 4/10 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | W. 171-194 | TBA | |
| Wed., 4/10 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | W 10-7 | 2:45 pm | inv 94535 |
| Wed., 4/10 | JV Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 2:45 pm | |
| Wed., 4/10 | V Boys Rugby | vs. Aspetuck | Home - Tiger Hollow Stadium [Directions] | 6:00 p.m. | Warm-ups on TH2 | |
| Wed., 4/10 | V Boys Tennis | Fairfield Ludlowe | Home - RHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/10 | V Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 3-0 | 2:30 pm | |
| Wed., 4/10 | JV Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Wed., 4/10 | V Softball | Stamford | Away - SHS Softball Field [Directions] | L 2-9 | 2:30 pm | |
| Wed., 4/10 | JV Softball | Stamford | Away - Cummings Park Field #4 [Directions] | 4:30 p.m. | 2:30 pm | |
| Wed., 4/10 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:30 pm | |
| Wed., 4/10 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 4/10 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 4/10 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/11 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | L 8-15 | 2:30 | |
| Thu., 4/11 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | W. 156-168 | 1:30 pm | at Tashua Knolls |
| Thu., 4/11 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 1:30 pm | at Tashua Knolls |
| Thu., 4/11 | V Boys Tennis | Greenwich | Home - RHS Tennis Courts [Directions] | L 2-5 | ||
| Thu., 4/11 | JV Boys Tennis | Greenwich | Home - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | 2:30 pm | |
| Thu., 4/11 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Thu., 4/11 | V Girls Golf | St. Joseph | Away [Directions] | Ridgefield 196 St.Joseph 242 | 1:30 p.m. | at Tashua Knolls |
| Thu., 4/11 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | W 9-3 | 2:30 pm | |
| Thu., 4/11 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | 2:30 pm | |
| Thu., 4/11 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:30 pm | |
| Thu., 4/11 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 4/11 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/11 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 4/12 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | W 2-0 | 1:45 pm | Pick up/drop off from ERMS |
| Fri., 4/12 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | L 0-6 | 1:45 pm | Pick up/drop off from ERMS |
| Fri., 4/12 | FR Baseball | Trumbull | Home - Branchville Civic (Playground Field) [Directions] | L 10-0(5) | ||
| Fri., 4/12 | V Softball | Trumbull | Home - Tiger Ridge Softball Field (RHS) [Directions] | L 3-7 | ||
| Fri., 4/12 | JV Softball | Trumbull | Home - RHS Upper Grass Field [Directions] | 4:15 p.m. | ||
| Fri., 4/12 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 4/12 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Fri., 4/12 | School Holidays and Closings | Early dismissal | ||||
| Sat., 4/13 | V Boys Lacrosse | Fairfield Warde | Home - Tiger Hollow Stadium [Directions] | W 9-6 | ||
| Sat., 4/13 | JV Boys Lacrosse | Fairfield Warde | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Sat., 4/13 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 4/13 | School Holidays and Closings | ACT Test | ||||
| Sun., 4/14 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-6pm | ||
| Sun., 4/14 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 4/14 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 4/15 | FR Girls Lacrosse | Wilton | Home - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 4/15 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Mon., 4/15 | School Holidays and Closings | Spring recess | ||||
| Tue., 4/16 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | L 2-8 | 11:30 am | Pick up/drop off from Governor Park (OHS) |
| Tue., 4/16 | FR Baseball | Danbury | Home - Branchville Civic (Playground Field) [Directions] | W 10-1 | ||
| Tue., 4/16 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | 2:30 pm | |
| Tue., 4/16 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 14-8 | 2:30 pm | |
| Tue., 4/16 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | 3:30 pm | |
| Tue., 4/16 | FR Girls Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | 9:30 am | |
| Tue., 4/16 | V Softball | Danbury | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 5-4 | ||
| Tue., 4/16 | JV Softball | Danbury | Home - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 4/16 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Tue., 4/16 | School Holidays and Closings | Spring recess | ||||
| Wed., 4/17 | V Baseball | Fairfield Ludlowe | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 2-1 | ||
| Wed., 4/17 | JV Baseball | Fairfield Ludlowe | Home - East Ridge MS [Directions] | W 11-1 (5 inn) | ||
| Wed., 4/17 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | W 4-0 | 2:30 pm | |
| Wed., 4/17 | FR Boys Lacrosse | Darien | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Rugby | Simsbury | Home - Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | V Softball | Fairfield Ludlowe | Away - Dougiello Field [Directions] | L 2-9 | 11 am | |
| Wed., 4/17 | JV Softball | Fairfield Ludlowe | Away - Dougiello Field [Directions] | 3:15 p.m. | 11 am | |
| Wed., 4/17 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 4/17 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 4/17 | School Holidays and Closings | Spring recess | ||||
| Thu., 4/18 | V Baseball | Greenwich | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 3-2 | ||
| Thu., 4/18 | JV Baseball | Greenwich | Home - East Ridge MS [Directions] | L 15-17 | ||
| Thu., 4/18 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | L 3-2 | 2:30 pm | 1 XL bus with storage - FR Baseball and V Softball |
| Thu., 4/18 | V Boys Lacrosse | Duxbury (MA) | Home - Tiger Hollow Stadium [Directions] | W 12-4 | ||
| Thu., 4/18 | JV Boys Lacrosse | Duxbury (MA) | Home - Tiger Hollow Turf Field II [Directions] | Cancelled | ||
| Thu., 4/18 | V Girls Lacrosse | Glastonbury | Home - Tiger Hollow Stadium [Directions] | W 16-6 | ||
| Thu., 4/18 | JV Girls Lacrosse | Glastonbury | Home - Tiger Hollow Stadium [Directions] | 12:15 p.m. | ||
| Thu., 4/18 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | W 15-8 | 2:30 pm | |
| Thu., 4/18 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 2:00 p.m. | 12 pm | |
| Thu., 4/18 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/18 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Thu., 4/18 | School Holidays and Closings | Spring recess | ||||
| Fri., 4/19 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 4/19 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Fri., 4/19 | School Holidays and Closings | Spring Recess - Good Friday, Passover begins at sundown | ||||
| Sat., 4/20 | V Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | W 21-4 | 11:15 am | |
| Sat., 4/20 | JV Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 3:00 p.m. | 1:30 pm | |
| Sat., 4/20 | FR Boys Lacrosse | Greenwich | Home - Tiger Hollow Turf Field II [Directions] | Cancelled | ||
| Sat., 4/20 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 4/20 | School Holidays and Closings | First day of Passover | ||||
| Sun., 4/21 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-6pm | ||
| Sun., 4/21 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 4/21 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 4/21 | School Holidays and Closings | Easter Sunday | ||||
| Mon., 4/22 | V Boys Golf | Stamford | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | W. 161-197 | ||
| Mon., 4/22 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | 2:30 pm | |
| Mon., 4/22 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Mon., 4/22 | V Girls Lacrosse | New Canaan | Home - Tiger Hollow Stadium [Directions] | L 6-5 | ||
| Mon., 4/22 | JV Girls Lacrosse | New Canaan | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 4/22 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 4/23 | V Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | L 1-2(8) | 2:30 pm | |
| Tue., 4/23 | JV Baseball | Brien McMahon | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 3-0 | ||
| Tue., 4/23 | FR Baseball | Brien McMahon | Home - East Ridge MS [Directions] | W 11-2 | ||
| Tue., 4/23 | V Boys Golf | New Canaan | Home - Silver Spring GC [Directions] | L. 157-155 | ||
| Tue., 4/23 | V Boys Lacrosse | Staples | Home - Tiger Hollow Stadium [Directions] | W 5-4 | ||
| Tue., 4/23 | JV Boys Lacrosse | Staples | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:30 p.m. | 1:45 pm | |
| Tue., 4/23 | V Boys Tennis | Wilton | Home - RHS Tennis Courts [Directions] | W 4-2 | ||
| Tue., 4/23 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:30 p.m. | 1:45 pm | |
| Tue., 4/23 | V Softball | Brien McMahon | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 8-1 | ||
| Tue., 4/23 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:30 pm | |
| Tue., 4/23 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 4/23 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-9pm | ||
| Tue., 4/23 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 4/24 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | W 12-2 | 1:30 pm | |
| Wed., 4/24 | V Boys Rugby | Darien | Away [Directions] | 4:30 p.m. | 2:45 pm | |
| Wed., 4/24 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 1-6 | 2:30 pm | |
| Wed., 4/24 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 4/24 | V Boys Volleyball | Trumbull | Home - RHS Main Gym [Directions] | L 1-3 | ||
| Wed., 4/24 | JV Boys Volleyball | Trumbull | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Ridgefield 191 Warde 199 | 1:30 pm | |
| Wed., 4/24 | JV Girls Golf | Fairfield Warde | Away [Directions] | 3:15 p.m. | at Smith Richardson GC | |
| Wed., 4/24 | FR Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | 3:45 pm | |
| Wed., 4/24 | V Softball | Bridgeport Central | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 16-1 | ||
| Wed., 4/24 | JV Softball | Bridgeport Central | Home - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Darien | Home - RHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Wed., 4/24 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 4/24 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/25 | V Boys Golf | Trinity Catholic | Home - Silver Spring GC [Directions] | W. 163-215 | ||
| Thu., 4/25 | V Boys Lacrosse | John Jay (NY) | Home - Tiger Hollow Stadium [Directions] | L 8-9(OT) | ||
| Thu., 4/25 | JV Boys Lacrosse | John Jay (NY) | Away | 4:30 p.m. | 3 pm | |
| Thu., 4/25 | JV Boys Tennis | Horace Greeley (NY) | Home - Yanity Tennis Courts [Directions] | 4:15 p.m. | ||
| Thu., 4/25 | V Girls Golf | New Canaan | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 190 New Canaan 166 | ||
| Thu., 4/25 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | L 12-14 | 2:30 pm | |
| Thu., 4/25 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | 2:30 pm | |
| Thu., 4/25 | V Softball | Darien | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 10-3 | ||
| Thu., 4/25 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 4/25 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 4/26 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 4/26 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 4/27 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 18-1 | 1 pm | |
| Sat., 4/27 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Sat., 4/27 | V Boys Outdoor Track | Penn Relays in Phildadelphia, PA | Away | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Volleyball | Rhody Invitational - CANCELLED | Away | Cancelled | ||
| Sat., 4/27 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 10-5 | 8:00 am | |
| Sat., 4/27 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 11:00 a.m. | 9:15 am | |
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays at Bethel HS | Away [Directions] | 9:00 a.m. | 7:30 am | |
| Sat., 4/27 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 4/27 | School Holidays and Closings | Last day of Passover | ||||
| Sun., 4/28 | V Boys Rugby | vs. Mid-State | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Sun., 4/28 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-4pm | ||
| Sun., 4/28 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 4/28 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 4/29 | V Baseball | Wilton | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 3-0 | ||
| Mon., 4/29 | JV Baseball | Wilton | Home - East Ridge MS [Directions] | W 5-1 | ||
| Mon., 4/29 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | W 6-3 | 2:30 pm | |
| Mon., 4/29 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | L. 171-148 | TBA | |
| Mon., 4/29 | JV Boys Golf | Darien | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Stamford | Home - Tiger Hollow Turf Field II [Directions] | Cancelled | ||
| Mon., 4/29 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 3-4 | 2:30 pm | |
| Mon., 4/29 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 4/29 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 2:30 pm | |
| Mon., 4/29 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | 2:30 pm | |
| Mon., 4/29 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Ridgefield 189 Ludlowe 187 | 1:30 pm | |
| Mon., 4/29 | V Girls Outdoor Track | Greenwich, Stamford | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 4/29 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | W 11-3 | 3 pm | |
| Mon., 4/29 | V Girls Tennis | Staples | Home - RHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Mon., 4/29 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 4/29 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 4/30 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | L 2-3(9) | 2:30 pm | |
| Tue., 4/30 | FR Baseball | Darien | Away - Darien JV Baseball field [Directions] | L 4-3 | ||
| Tue., 4/30 | JV Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | TBA | Country Club of Darien |
| Tue., 4/30 | V Boys Lacrosse | Yorktown (NY) | Away | W 12-11 | 5 pm | |
| Tue., 4/30 | JV Boys Lacrosse | Yorktown (NY) | Away | 4:30 p.m. | 2:30 pm | |
| Tue., 4/30 | V Boys Outdoor Track | Greenwich, Stamford | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Golf | Wilton | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 201 Wilton 216 | ||
| Tue., 4/30 | V Girls Lacrosse | Fairfield Warde | Home - Tiger Hollow Stadium [Directions] | W 12 - 3 | Autism Awareness Game | |
| Tue., 4/30 | JV Girls Lacrosse | Fairfield Warde | Home - Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | 2:30 pm | |
| Tue., 4/30 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 4/30 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 5/1 | V Boys Golf | Staples | Away - Longshore [Directions] | L. 156-149 | 1:30 pm | |
| Wed., 5/1 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | TBA | Longshore Country Club |
| Wed., 5/1 | FR Boys Lacrosse | New Canaan | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 5:00 p.m. | 3:45 pm | |
| Wed., 5/1 | V Boys Volleyball | Fairfield Warde | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/1 | JV Boys Volleyball | Fairfield Warde | Home - RHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | FR Girls Lacrosse | New Canaan | Home - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Girls Tennis | Weston | Home - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 5/1 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/2 | JV Baseball | Danbury | Away - Danbury HS Junior Varsity Baseball Field [Directions] | W 10-2 | 2:30 pm | |
| Thu., 5/2 | FR Baseball | Staples | Home - East Ridge MS [Directions] | W 5-4 | ||
| Thu., 5/2 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | L. 172-163 | TBA | |
| Thu., 5/2 | V Boys Lacrosse | Westhill | Home - Tiger Hollow Stadium [Directions] | W 19-1 | Senior Night | |
| Thu., 5/2 | JV Boys Lacrosse | Westhill | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Boys Tennis | New Canaan | Home - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Golf | Greenwich | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 187 Greenwich 189 | ||
| Thu., 5/2 | JV Girls Golf | Greenwich | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Newtown | Home - Tiger Hollow Stadium [Directions] | W 12-10 | ||
| Thu., 5/2 | JV Girls Lacrosse | Newtown | Home - Tiger Hollow Turf Field II [Directions] | 6:00 p.m. | ||
| Thu., 5/2 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:30 pm | |
| Thu., 5/2 | JV Girls Tennis | New Canaan | Away - TBD [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 5/2 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/2 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 5/3 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | L 0-2 | 2:30 pm | 1 XL bus with storage V/JV Baseball |
| Fri., 5/3 | JV Baseball | Staples | Away - Wakeman Field [Directions] | L 6-9 | 2:30 pm | 1 XL bus with storage V/JV Baseball |
| Fri., 5/3 | V Boys Outdoor Track | Night of 3200's in Holmdel, NJ | Away | 6:00 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Stamford | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Fri., 5/3 | JV Boys Volleyball | Stamford | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 5/3 | V Girls Outdoor Track | Somers NY Invitational | Away | TBA | TBA | |
| Fri., 5/3 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 5/3 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 5/4 | FR Boys Lacrosse | Trumbull | Home - Tiger Hollow Stadium [Directions] | 11:30 a.m. | ||
| Sat., 5/4 | V Boys Tennis | New Canaan | Home - RHS Tennis Courts [Directions] | L 3-4 | ||
| Sat., 5/4 | V Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | W 14-2 | 2:30 pm | |
| Sat., 5/4 | JV Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | 5:30 p.m. | 4:00 pm | |
| Sat., 5/4 | V Girls Outdoor Track | Somers NY Invitational | Away | TBA | 8:30 am | pick up at 3 pm/ inv 97634 |
| Sat., 5/4 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 5/4 | School Holidays and Closings | SAT Test | ||||
| Sun., 5/5 | V Boys Rugby | vs. West Hartford | Home - Tiger Hollow Stadium [Directions] | 6:00 p.m. | ||
| Sun., 5/5 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-4pm | ||
| Sun., 5/5 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 5/5 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Sun., 5/5 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 p.m.-10pm | ||
| Mon., 5/6 | V Baseball | St. Joseph | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 4-2 | ||
| Mon., 5/6 | JV Baseball | St. Joseph | Home - East Ridge MS [Directions] | L 1-10 | ||
| Mon., 5/6 | JV Boys Golf | Darien | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Staples | Home - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Bridgeport Central, Westhill | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Norwalk | Home - RHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 5/6 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | 2:30 pm | |
| Mon., 5/6 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | 2:30 pm | |
| Mon., 5/6 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Ridgefield 195 New Canaan 169 | 2 pm | |
| Mon., 5/6 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | 4 pm | |
| Mon., 5/6 | V Girls Outdoor Track | Bridgeport Central, Westhill | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | St. Joseph | Away - Unity Park, Trumbull [Directions] | L 1-9 | 2:30 pm | |
| Mon., 5/6 | JV Softball | St. Joseph | Away - Long Hill Administration field, Trumbull CT [Directions] | 4:30 p.m. | 2:30 pm | |
| Mon., 5/6 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | W 6-1 [Detailed Results] | 2:30 pm | |
| Mon., 5/6 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 5/6 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 5/7 | V Boys Golf | Greenwich | Home - Ridgewood Country Club [Directions] | L. 152-163 | ||
| Tue., 5/7 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 16-6 | 4 pm | |
| Tue., 5/7 | JV Boys Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 5/7 | V Boys Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | W 4-3 | 2:30 pm | |
| Tue., 5/7 | JV Boys Tennis | Horace Greeley (NY) | Home - Yanity Tennis Courts [Directions] | 4:15 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Westhill | Home - RHS Tennis Courts [Directions] | L 3-4 | ||
| Tue., 5/7 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-8pm | ||
| Tue., 5/7 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-9pm | ||
| Tue., 5/7 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 5/8 | V Baseball | New Canaan | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 3-4 | ||
| Wed., 5/8 | JV Baseball | New Canaan | Home - East Ridge MS [Directions] | L 3-5 | ||
| Wed., 5/8 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | L 4-2 | 2:30 pm | |
| Wed., 5/8 | V Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | W. 169-195 | tba | |
| Wed., 5/8 | V Boys Rugby | Greenwich | Away [Directions] | 4:30 p.m. | 2:30 pm | JV Game |
| Wed., 5/8 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 6-1 | 2:30 pm | |
| Wed., 5/8 | V Boys Volleyball | St. Joseph | Home - RHS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/8 | JV Boys Volleyball | St. Joseph | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Golf | Trumbull | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 198 Trumbull 207 | ||
| Wed., 5/8 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | W 9-2 | 4:45 pm | |
| Wed., 5/8 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 5/8 | V Girls Tennis | Brien McMahon | Home - RHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 5/8 | JV Girls Tennis | Darien | Home - Yanity Tennis Courts [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 5/8 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/9 | V Baseball | Norwalk | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 3-9 | Senior Day | |
| Thu., 5/9 | V Boys Golf | Westhill | Away - E. Gaynor Brennan Golf Course [Directions] | T. 163-163 | tba | |
| Thu., 5/9 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | W 10-7 | 4 pm | inv 97628 |
| Thu., 5/9 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 2:30 pm | inv 97628 |
| Thu., 5/9 | V Boys Outdoor Track | Loucks Games in White Plains, NY | Away | 5:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 5-2 | 2:30 pm | |
| Thu., 5/9 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 5/9 | JV Girls Golf | Fairfield Warde, Fairfield Ludlowe | Away [Directions] | 3:15 p.m. | 1:30 pm | |
| Thu., 5/9 | V Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | W 18-3 | 3:45 pm | |
| Thu., 5/9 | JV Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 5/9 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | W 8-3 | 3:15 pm | |
| Thu., 5/9 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:30 p.m. | 3:15 pm | |
| Thu., 5/9 | JV Girls Tennis | Fairfield Warde | Home - RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-8pm | ||
| Thu., 5/9 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-9pm | ||
| Thu., 5/9 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 5/10 | FR Boys Lacrosse | Wilton | Home - Tiger Hollow Turf Field II [Directions] | Cancelled | ||
| Fri., 5/10 | V Boys Outdoor Track | Loucks Games in White Plains, NY | Away | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 0-3 | 2:30 pm | |
| Fri., 5/10 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | 2:30 pm | |
| Fri., 5/10 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 5/10 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 5/11 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 20-0 | 2:15 pm | |
| Sat., 5/11 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:00 p.m. | 11:30 am | |
| Sat., 5/11 | V Boys Outdoor Track | Loucks Games in White Plains, NY | Away | 9:00 a.m. | ||
| Sat., 5/11 | V Boys Tennis | St. Joseph | Away - St. Joseph HS [Directions] | W 7-0 | 10 am | |
| Sat., 5/11 | V Softball | Staples | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 7-3 | ||
| Sat., 5/11 | JV Softball | Staples | Home - RHS Upper Grass Field [Directions] | 11:00 a.m. | ||
| Sat., 5/11 | V Girls Tennis | St. Joseph | Away [Directions] | L 3-4 | 10am | |
| Sat., 5/11 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 5/12 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-4pm | ||
| Sun., 5/12 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 5/12 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 5/12 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Sun., 5/12 | School Holidays and Closings | Mothers Day | ||||
| Mon., 5/13 | FR Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 5/13 | V Boys Rugby | Greenwich | Home - Tiger Hollow Stadium [Directions] | 6:30 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | W 3-1 | ||
| Mon., 5/13 | JV Boys Volleyball | Fairfield Ludlowe | Home - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Fairfield Warde | Home - Hardscrabble Club, 22 Sutton Place, Brewster NY [Directions] | L 3-4 | 12:30 pm | |
| Mon., 5/13 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 5/13 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Tue., 5/14 | FR Baseball | Westhill | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 11-0 | ||
| Tue., 5/14 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 14-2 | 5 pm | |
| Tue., 5/14 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | 3:15 pm | |
| Tue., 5/14 | V Boys Outdoor Track | Danbury | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Boys Tennis | Darien | Home - RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-0 | 2:30 pm | |
| Tue., 5/14 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | 2:30 pm | |
| Tue., 5/14 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | W 10-8 | 4:30 pm | |
| Tue., 5/14 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 5/14 | V Girls Outdoor Track | Danbury | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Westhill | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 15-3 | ||
| Tue., 5/14 | JV Softball | Westhill | Home - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Tennis | FCIAC Tournament Qtr Finals | Away | 4:00 p.m. | ||
| Tue., 5/14 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 5/14 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-9pm | ||
| Tue., 5/14 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 5/15 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 1-2 | 1:45 pm | |
| Wed., 5/15 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | W 9-0 | 1:45 pm | |
| Wed., 5/15 | FR Baseball | Fairfield Warde | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 10-2 | ||
| Wed., 5/15 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | W. 174-179 | 2:30 pm | inv 101064 |
| Wed., 5/15 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | 2:30 pm | inv 101064 |
| Wed., 5/15 | V Boys Tennis | Greenwich | Away - TBA [Directions] | L 4-1 | 2:30 pm | FCIAC Tournament Qtr Finals at Greenwich |
| Wed., 5/15 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 2:30 pm | |
| Wed., 5/15 | V Girls Lacrosse | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | W 14-6 | Senior Night | |
| Wed., 5/15 | JV Girls Lacrosse | Brien McMahon | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Trumbull | Home - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Softball | Fairfield Warde | Home - Tiger Ridge Softball Field (RHS) [Directions] | W 1-0 | ||
| Wed., 5/15 | JV Softball | Fairfield Warde | Home - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 5/15 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/16 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | W 6-2 | 2:30 pm | |
| Thu., 5/16 | JV Baseball | Westhill | Home - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | W 8-3 | ||
| Thu., 5/16 | V Boys Golf | Fairfield Ludlowe | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | W. 164-160 | ||
| Thu., 5/16 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 2:45 pm | |
| Thu., 5/16 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 5/16 | V Girls Tennis | FCIAC Tournament Semi Finals | Away | 4:00 p.m. | ||
| Thu., 5/16 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-8pm | ||
| Thu., 5/16 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/16 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Thu., 5/16 | Unified Sports Volleyball | Oxford Tournament | Away | Cancelled | ||
| Fri., 5/17 | V Baseball | FCIAC Tournament Qtr Finals | Away | 4:00 p.m. | ||
| Fri., 5/17 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | W 6-3 | 2:30 pm | |
| Fri., 5/17 | FR Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | W 1-0(11) | 2:30 pm | |
| Fri., 5/17 | V Boys Outdoor Track | Hatter Freshman Invitational at New Milford HS | Away | 4:00 p.m. | ||
| Fri., 5/17 | V Boys Outdoor Track | Dream Invitational at New Milford HS | Away | 8:00 p.m. | ||
| Fri., 5/17 | V Boys Tennis | FCIAC Tournament Semi Finals | Away | 4:00 p.m. | ||
| Fri., 5/17 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-1 | 2:30 pm | |
| Fri., 5/17 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | 2:30 pm | |
| Fri., 5/17 | V Girls Lacrosse | Wilton | Home - Tiger Hollow Stadium [Directions] | L 12-6 | FCIAC Tournament Qtr Finals | |
| Fri., 5/17 | V Softball | Stamford | Away - SHS Softball Field [Directions] | L 10-7 | 2:30 pm | |
| Fri., 5/17 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 5/17 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 5/18 | V Boys Lacrosse | Fairfield Warde | Home [Directions] | W 15-7 | FCIAC Tournament Qtr Finals | |
| Sat., 5/18 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 5/18 | School Holidays and Closings | Junior Prom | ||||
| Sun., 5/19 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-4pm | ||
| Sun., 5/19 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 5/19 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 5/19 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Mon., 5/20 | V Baseball | FCIAC Tournament Semi Finals at Cubeta Stadium | Away | TBA | ||
| Mon., 5/20 | V Boys Volleyball | FCIAC Tournament Playdowns | Away | 4:00 p.m. | ||
| Mon., 5/20 | V Girls Golf | Staples | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Cancelled | ||
| Mon., 5/20 | JV Girls Golf | Staples | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ||
| Mon., 5/20 | V Girls Lacrosse | FCIAC Tournament Semi Finals at Norwalk HS | Away | TBA | ||
| Mon., 5/20 | V Softball | FCIAC Tournament Semi Finals at Sacred Heart University | Away | TBA | ||
| Mon., 5/20 | V Girls Tennis | FCIAC Tournament Finals at Wilton HS | Away | 4:00 p.m. | ||
| Mon., 5/20 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 5/20 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Mon., 5/20 | Unified Sports Volleyball | Unified vs. Faculty game | Home - RHS Main Gym [Directions] | 2:30 p.m.-3:30pm | ||
| Tue., 5/21 | JV Boys Golf | Brien McMahon | Away [Directions] | 3:15 p.m. | tba | Oak Hills GC |
| Tue., 5/21 | V Boys Lacrosse | New Canaan | Away [Directions] | L 11-10 | 3:15 pm | FCIAC Tournament Semi Finals at Brien McMahon |
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championships at Southern CT State University | Away | 1:30 p.m. | 10:30 am | |
| Tue., 5/21 | V Boys Rugby | vs. Fairfield | Away | 4:30 p.m. | 2:45 pm | at Sacred Heart University turf field |
| Tue., 5/21 | V Boys Tennis | FCIAC Finals at Wilton HS | Away | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Golf | Staples | Away - Longshore [Directions] | Ridgefield 197 Staples 193 | 1:30 pm | |
| Tue., 5/21 | JV Girls Golf | Staples | Away [Directions] | 3:00 p.m. | tba | at Longshore |
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Finals at SCSU | Away | 1:30 p.m. | 10:30 am | |
| Tue., 5/21 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-8pm | ||
| Tue., 5/21 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 5/21 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 5/22 | V Baseball | FCIAC Tournament Finals at Cubeta Stadium | Away | 7:00 p.m. | ||
| Wed., 5/22 | V Boys Golf | Fairfield Prep | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | W. 158-165 (Match was played on the back nine) | ||
| Wed., 5/22 | V Boys Volleyball | FCIAC Tournament Semi Finals at Fairfield Ludlowe | Away | TBA | ||
| Wed., 5/22 | V Girls Golf | Darien | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 185 Darien 198 | ||
| Wed., 5/22 | JV Girls Golf | Darien | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 2:30 p.m. | ||
| Wed., 5/22 | V Girls Lacrosse | FCIAC Tournament Finals at Norwalk HS | Away | 7:00 p.m. | ||
| Wed., 5/22 | V Softball | Brookfield (Scrim.) | Away - BHS Softball Field [Directions] | 3:30 p.m. | 2:30 pm | |
| Wed., 5/22 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 5/22 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/23 | V Boys Golf | CHAPPA Tournament at Longshore | Away | 8:00 a.m. | tba | CHAPPA Tournament at Longshore |
| Thu., 5/23 | JV Boys Golf | Fairfield Warde | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | ||
| Thu., 5/23 | V Boys Lacrosse | FCIAC Tournament Finals at Brien McMahon | Away | 7:00 p.m. | ||
| Thu., 5/23 | V Boys Rugby | Tournament Game- Opponent Not Known | Home - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/23 | V Softball | FCIAC Tournament Finals at Sacred Heart | Away | 5:00 p.m. | ||
| Thu., 5/23 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-8pm | ||
| Thu., 5/23 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/23 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - Hall HS [Directions] | 8:30 a.m. | ||
| Fri., 5/24 | V Boys Volleyball | FCIAC Tournament Finals at Fairfield Ludlow | Away | 7:00 p.m. | ||
| Fri., 5/24 | V Girls Tennis | CIAC Tourney Qualifying Round | Away - Highest Seed | TBA | ||
| Fri., 5/24 | Miscellaneous Events | RHS Movie Night | - Tiger Hollow Stadium | 7:00 p.m.-10:30pm | ||
| Fri., 5/24 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 5/25 | V Baseball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | qualified | |
| Sat., 5/25 | V Boys Lacrosse | CIAC Tourney Qualifying Round | Home - Higher Seed [Directions] | TBA | qualified for state tournament | |
| Sat., 5/25 | V Boys Tennis | CIAC Tourney Through Quarterfinals | Away - Hall HS [Directions] | TBA | ||
| Sat., 5/25 | V Girls Lacrosse | CIAC Tourney Qualifying Round | Home - Higher Seed [Directions] | TBA | qualified for state tournament | |
| Sat., 5/25 | V Softball | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | ||
| Sat., 5/25 | V Girls Tennis | CIAC Tourney 1st Rounds | Away - Highest Seed | TBA | ||
| Sat., 5/25 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 5/26 | Miscellaneous Events | CT Rugby State Championships | Home - Tiger Hollow Stadium [Directions] | 10:00 a.m.-7pm | ||
| Sun., 5/26 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 5/27 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Mon., 5/27 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 7:30 p.m.-9:00 p.m. | ||
| Mon., 5/27 | School Holidays and Closings | Memorial Day - school closed | ||||
| Tue., 5/28 | V Boys Golf | St. Joseph | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | W. 163-201 | ||
| Tue., 5/28 | V Boys Golf | Holohan Tournament at Darien | Away | TBA | Holohan Tournament at Darien | |
| Tue., 5/28 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Lacrosse | Glastonbury | Away - GHS Turf Field [Directions] | W 13-5 | 1:45 pm | CIAC Tourney 1st Round |
| Tue., 5/28 | V Girls Tennis | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Tue., 5/28 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Tue., 5/28 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 5/29 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | L 1-2 | 1:30 pm | CIAC Tourney 1st Round |
| Wed., 5/29 | V Boys Lacrosse | Trumbull | Home - Tiger Hollow Stadium [Directions] | W 16-4 | ||
| Wed., 5/29 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | TBA | 1st Student inv 105955 279.24 (continuation of rainout on 5/29) |
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 3-0 | 3 pm | CIAC Tourney 1st Round |
| Wed., 5/29 | V Girls Golf | Danbury | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 222 Danbury 230 | ||
| Wed., 5/29 | JV Girls Golf | Danbury | Home - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | TBA | 1st Student inv 105955 279.23 - rainout |
| Wed., 5/29 | V Softball | Greenwich | Away - Higher Seed [Directions] | W 13-12 | 1:15 pm | CIAC Tourney 1st Round |
| Wed., 5/29 | V Girls Tennis | CIAC Tourney Semifinals | Away - Higher Seed | TBA | ||
| Wed., 5/29 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 5/29 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/30 | V Baseball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Thu., 5/30 | V Boys Golf | FCIAC Tournament at Fairchild Wheeler | Away | 12:30 p.m. | tba | FCIAC Tournament at Fairchild Wheeler |
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Golf | FCIAC Tournament Finals at Fairchild Wheeler | Away | 9:00 a.m. | 7:15 am | conf 49417 |
| Thu., 5/30 | V Girls Lacrosse | Cheshire | Away - Cheshire High Main Game field [Directions] | W 13-4 | 2:30 pm | |
| Thu., 5/30 | V Girls Tennis | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Thu., 5/30 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Thu., 5/30 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 5/31 | V Boys Volleyball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Fri., 5/31 | V Softball | West Haven | Away - Higher Seed [Directions] | W 5-0 | 10:15 am | |
| Fri., 5/31 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 5/31 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Fri., 5/31 | School Holidays and Closings | Senior Prom | ||||
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 6/1 | V Boys Lacrosse | Staples | Home - Higher Seed [Directions] | L 8-6 | ||
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 12:00 p.m. | ||
| Sat., 6/1 | V Softball | Southington | Away - Higher Seed [Directions] | L 3-2 | 12:45 pm | |
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | ||
| Sat., 6/1 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-1pm | ||
| Sat., 6/1 | Miscellaneous Events | Relay under the Lights | - Tiger Hollow Stadium | 6:30 p.m.-9:30pm | ||
| Sat., 6/1 | School Holidays and Closings | SAT Test | ||||
| Sun., 6/2 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-2pm | ||
| Sun., 6/2 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 6/2 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 6/2 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | TBA | |
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Mon., 6/3 | V Girls Lacrosse | New Canaan | Away - Site TBA [Directions] | L 8-5 | 5 pm | CIAC Tourney Semifinals at Brien McMahon |
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | TBA | |
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | ||
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 6/4 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 8:00 a.m. | tba | |
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 6/4 | V Boys Volleyball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | 7:15 am | conf 49418 |
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | ||
| Tue., 6/4 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Tue., 6/4 | School Holidays and Closings | Senior Awards | ||||
| Wed., 6/5 | V Boys Lacrosse | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Wed., 6/5 | V Girls Golf | Guimares Tournament at Heritage Golf Course | Away | 1:00 p.m. | ||
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Wed., 6/5 | Miscellaneous Events | Westchester Elite | - Tiger Hollow and Tiger Hollow 2 | 4:00 p.m.-6pm | ||
| Wed., 6/5 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Wed., 6/5 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Wed., 6/5 | School Holidays and Closings | Life After Academics | ||||
| Thu., 6/6 | V Boys Volleyball | CIAC Tourney Final | Away - Site TBA | 7:00 p.m. | ||
| Thu., 6/6 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Thu., 6/6 | School Holidays and Closings | Senior Banquet | ||||
| Fri., 6/7 | Miscellaneous Events | Charity Soccer | - Tiger Hollow Turf Field II | 2:15 p.m.-4:30pm | ||
| Fri., 6/7 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Fri., 6/7 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 7:00 p.m.-9pm | ||
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | TBA | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Lacrosse | CIAC Tourney Final | Away - Brien McMahon HS [Directions] | TBA | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Girls Lacrosse | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 6/8 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sat., 6/8 | School Holidays and Closings | ACT Test | ||||
| Sun., 6/9 | Miscellaneous Events | RYL | - Tiger Hollow Stadium | 10:00 a.m.-4pm | ||
| Sun., 6/9 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 10:00 a.m.-6pm | ||
| Sun., 6/9 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 6/9 | Miscellaneous Events | P&R Track Meet | Home - Tiger Hollow Stadium [Directions] | 8:00 a.m.-12pm | ||
| Sun., 6/9 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Tue., 6/11 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-7pm | ||
| Tue., 6/11 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/12 | Miscellaneous Events | Westchester Elite | - Tiger Hollow Stadium | 4:00 p.m.-6pm | ||
| Wed., 6/12 | Miscellaneous Events | Westchester Elite Shirts vs Skirts | - Tiger Hollow Stadium | 6:00 p.m.-9pm | ||
| Thu., 6/13 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 6:00 p.m.-7pm | ||
| Thu., 6/13 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 6/14 | School Holidays and Closings | Last Day of School - tentative | ||||
| Sun., 6/16 | Miscellaneous Events | Fathers' Day 5K | Home - Tiger Hollow Stadium [Directions] | 6:00 a.m.-11am | ||
| Sun., 6/16 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 6/16 | Miscellaneous Events | Westchester Elite | Home - Scotts Ridge MS Turf [Directions] | 9:00 a.m.-12pm | ||
| Sun., 6/16 | Miscellaneous Events | RYL | - Tiger Hollow Turf Field II | 9:00 a.m.-12pm | ||
| Sun., 6/16 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Sun., 6/16 | School Holidays and Closings | Fathers Day | ||||
| Mon., 6/17 | Miscellaneous Events | RYF Flag Tournament | - Tiger Hollow Stadium | 5:00 p.m.-8pm | ||
| Mon., 6/17 | Miscellaneous Events | RYF Flag Tournament | - Tiger Hollow Turf Field II | 5:00 p.m.-8pm | ||
| Mon., 6/17 | Miscellaneous Events | SCOREBOARD INSTALL | Home - RHS Main and Aux Gyms [Directions] | TBA | ||
| Tue., 6/18 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Tue., 6/18 | Miscellaneous Events | SCOREBOARD INSTALL | Home - RHS Main and Aux Gyms [Directions] | TBA | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | Miscellaneous Events | Westchester Elite | - Tiger Hollow and Tiger Hollow 2 | 4:00 p.m.-6pm | ||
| Wed., 6/19 | Miscellaneous Events | SCOREBOARD INSTALL | Home - RHS Main and Aux Gyms [Directions] | TBA | ||
| Thu., 6/20 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Fri., 6/21 | School Holidays and Closings | Graduation | ||||
| Sun., 6/23 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Sun., 6/23 | Miscellaneous Events | SCOR | Home - Tiger Hollow Stadium [Directions] | 4:00 p.m.-6pm | ||
| Mon., 6/24 | Miscellaneous Events | Westchester Elite | - Scotts Ridge MS Turf | 5:00 p.m.-6:30pm | ||
| Tue., 6/25 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Wed., 6/26 | Miscellaneous Events | Westchester Elite | - Tiger Hollow and Tiger Hollow 2 | 5:00 p.m.-7pm | ||
| Thu., 6/27 | Miscellaneous Events | RAMS | - Tiger Hollow Stadium | 8:00 p.m.-10pm | ||
| Sun., 6/30 | Miscellaneous Events | RAMS | - Tiger Hollow Turf Field II | 8:00 a.m.-10am | ||
| Mon., 7/1 | Miscellaneous Events | Westchester Elite | - Scotts Ridge MS Turf | 5:00 p.m.-6:30pm | ||
| Mon., 7/8 | Miscellaneous Events | Westchester Elite | - Scotts Ridge MS Turf | 5:00 p.m.-6:30pm | ||
| Wed., 7/10 | Miscellaneous Events | Westchester Elite | - Tiger Hollow and Tiger Hollow 2 | 5:00 p.m.-7pm | ||
| Sat., 7/13 | School Holidays and Closings | ACT Test | ||||
| Mon., 7/15 | Miscellaneous Events | Westchester Elite | - Scotts Ridge MS Turf | 5:00 p.m.-6:30pm | ||
| Wed., 7/17 | Miscellaneous Events | Westchester Elite | - Tiger Hollow and Tiger Hollow 2 | 5:00 p.m.-7pm | ||
| Sat., 8/10 | Miscellaneous Events | Ryan Meegan Memorial Soccer Game | Home - Tiger Hollow Stadium [Directions] | 5:00 p.m.-7pm | ||