| Fairfield Ludlowe 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 915 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Wilton | Home - Tunxis Hill Park [Directions] | 4:30 p.m. | Shuttle | |
| TBA | JV Baseball | Joel Barlow | Home - Kiwanis Field [Directions] | TBA | ||
| TBA | FR Baseball | Joel Barlow | Away - Boys & Girls Club of Easton/Redding [Directions] | TBA | Ride with Varsity | |
| TBA | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| TBA | V Co-ed Alpine Skiing | State Tournament | Away - Mt. Southington | TBA | TBA | |
| TBA | V Co-ed Sailing | Stamford | Home [Directions] | 3:30 p.m. | Also Vs. Fairfield Prep | |
| TBA | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | TBA | Ride with Varsity | |
| TBA | FR Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | TBA | PU:2:30 RE:5:30 | |
| TBA | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | PU:2:10 RE:5:15 | |
| TBA | JV Girls Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | TBA | PU:2:45 RE:5:00 | |
| TBA | JV Girls Soccer | Brien McMahon | Home - Sturges Park [Directions] | TBA | ||
| TBA | JV Girls Soccer | Westhill | Home - Sturges Park [Directions] | TBA | ||
| TBA | JV Softball | Fairfield Warde | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | TBA | PU:2:30 RE:5:30 | |
| TBA | JV Softball | Stamford | Away - Cummings Park [Directions] | TBA | Ride with Varsity | |
| TBA | JV Softball | Brien McMahon | Home - Tom Haydon Field [Directions] | Cancelled | ||
| TBA | JV Softball | Danbury | Home - Tom Haydon Field [Directions] | TBA | ||
| TBA | JV Girls Tennis | Lauralton Hall | Home - Dwight Elementary School [Directions] | 3:30 p.m. | ||
| TBA | JV Girls Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:30 p.m. | ||
| Mon., 8/28 | V Girls Soccer | Notre Dame-Fairfield (Scrim.) | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Newtown (Scrim.) | Away - Treadwell Town Park [Directions] | 4:30 p.m. | PU:2:45 RE:6:00 | |
| Tue., 8/29 | V Field Hockey | Guilford (Scrim.) | Away - Kavanaugh Turf Field at GHS [Directions] | 3:00 p.m. | PU:12:30 RE:5:30 | |
| Tue., 8/29 | JV Field Hockey | Guilford (Scrim.) | Away [Directions] | 3:00 p.m. | Ride with Varsity | |
| Tue., 8/29 | V Girls Volleyball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 4:45 p.m. | PU:2:00 RE:6:00 | |
| Tue., 8/29 | JV Girls Volleyball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:15 p.m. | Ride with Varsity | |
| Tue., 8/29 | FR Girls Volleyball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:15 p.m. | Ride with Varsity | |
| Thu., 8/31 | V Boys Soccer | Fairfield Prep (Scrim.) | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | V Football | Bullard/Kolbe (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Sat., 9/2 | V Field Hockey | Convent of Sacred Heart (Scrim.) | Away | 9:00 a.m. | PU:7:30 RE:2:00 | |
| Sat., 9/2 | V Girls Soccer | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 1:30 p.m. | PU:11:00 RE:2:45 | |
| Sat., 9/2 | JV Girls Soccer | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 12:00 p.m. | Ride with Varsity | |
| Sat., 9/2 | V Girls Volleyball | Glastonbury Jamboree | Away | 1:30 p.m. | PU:11:30 RE:6:00 | |
| Tue., 9/5 | V Boys Cross Country | Bethel (Scrim.) | Away [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Tue., 9/5 | V Girls Cross Country | Bethel (Scrim.) | Away [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Tue., 9/5 | V Field Hockey | Bethel (Scrim.) | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | V Boys Soccer | Stamford | Home - Taft Field [Directions] | W 1-0 | ||
| Fri., 9/8 | JV Boys Soccer | Stamford | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | FR Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 9/8 | V Field Hockey | Wilton | Home - Taft Field [Directions] | W 1 - 0 | ||
| Fri., 9/8 | JV Field Hockey | Wilton | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Fri., 9/8 | FR Field Hockey | Wilton | Away - Wilton HS - Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 9/8 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | L 0-3 | PU:2:30 RE:7:00 | |
| Fri., 9/8 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 3:45 p.m. | Ride with Varsity | |
| Sat., 9/9 | V Football | Westhill | Away - Westhill Football Field [Directions] | L 27-50 | PU:10:30 RE:3:30 (2 buses) | |
| Sat., 9/9 | V Competitive Cheerleading | Westhill | Away [Directions] | 1:30 p.m. | PU:12:00 RE:3:30 | |
| Sat., 9/9 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 3-1 | PU:8:15 RE:1:30 | |
| Sat., 9/9 | JV Girls Soccer | Stamford | Away - Stamford HS [Directions] | 12:00 p.m. | Ride with Varsity | |
| Mon., 9/11 | V Boys Cross Country | Fairfield Warde, Darien | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | JV Football | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 9/11 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | T 2-2 | PU:5:00 RE:8:00 | |
| Mon., 9/11 | JV Boys Soccer | Brien McMahon | Away - BMHS Field 2 [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| Mon., 9/11 | FR Boys Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 9/11 | V Girls Cross Country | Fairfield Warde, Darien | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Field Hockey | Stamford | Home - Taft Field [Directions] | W 3 - 0 | ||
| Tue., 9/12 | JV Field Hockey | Stamford | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Brien McMahon | Home - Taft Field [Directions] | T 0-0 | ||
| Tue., 9/12 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | PU:1:30 RE:4:30 | |
| Wed., 9/13 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | T 0-0 | PU:2:30 RE:5:30 | |
| Wed., 9/13 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 9/13 | FR Boys Soccer | Danbury | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | W 3-2 | ||
| Wed., 9/13 | JV Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Thu., 9/14 | FR Football | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/14 | V Field Hockey | St. Joseph | Home - Taft Field [Directions] | W 10 - 1 | ||
| Thu., 9/14 | JV Field Hockey | St. Joseph | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Danbury | Home - Sturges Park [Directions] | T 1-1 | ||
| Thu., 9/14 | JV Girls Soccer | Danbury | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/14 | V Girls Swimming and Diving | Staples | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Football | Trumbull | Home - Taft Field [Directions] | L 0-33 | ||
| Fri., 9/15 | V Boys Soccer | Greenwich | Home - Roger Ludlowe MS [Directions] | W 3-2 | ||
| Fri., 9/15 | JV Boys Soccer | Greenwich | Home - Sturges Park [Directions] | 4:30 p.m. | ||
| Fri., 9/15 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | W 1-0 | PU:2:30 RE:6:00 | |
| Fri., 9/15 | JV Girls Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | Ride with Varsity | |
| Fri., 9/15 | FR Girls Soccer | Greenwich | Home - South Pine Creek Field [Directions] | 4:30 p.m. | ||
| Fri., 9/15 | V Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | L 2-3 | ||
| Fri., 9/15 | JV Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | FR Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Sat., 9/16 | V Boys Cross Country | Wilton Invitational | Away | 9:30 a.m. | PU:8:00 RE:11:00 | |
| Sat., 9/16 | JV Football | Trumbull | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 9/16 | FR Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | PU:8:45 RE:11:30 | |
| Sat., 9/16 | V Girls Cross Country | Wilton Invitational | Away | 9:30 a.m. | PU:8:00 RE:11:00 | |
| Mon., 9/18 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-3 | PU:4:00 RE:7:30 | |
| Mon., 9/18 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 9/18 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 1-3 | PU:2:30 RE:6:30 | |
| Mon., 9/18 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | Ride with Varsity | |
| Tue., 9/19 | V Boys Cross Country | Stamford, Trumbull, Westhill | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Ridgefield | Home - Taft Field [Directions] | L 0-3 | ||
| Tue., 9/19 | JV Boys Soccer | Ridgefield | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 9/19 | V Girls Cross Country | Stamford, Trumbull, Westhill | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | L 4 - 1 | PU:2:30 RE:6:30 | |
| Tue., 9/19 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | Ride with Varsity | |
| Tue., 9/19 | FR Field Hockey | Staples | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | PU:2:00 RE:5:00 | |
| Tue., 9/19 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 1-3 | PU:2:30 RE:6:30 | |
| Tue., 9/19 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Tue., 9/19 | FR Girls Volleyball | Danbury | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | L 21-41 | PU:4:30 RE:9:00 (2 buses) | |
| Fri., 9/22 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | W 3-0 | PU:2:30 RE:5:30 | |
| Fri., 9/22 | JV Boys Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 9/22 | FR Boys Soccer | Trumbull | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Competitive Cheerleading | Norwalk | Away [Directions] | 7:00 p.m. | PU:5:30 RE:9:00 | |
| Fri., 9/22 | V Field Hockey | Greenwich | Home - Taft Field [Directions] | L 4 - 2 | ||
| Fri., 9/22 | JV Field Hockey | Greenwich | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | FR Girls Soccer | Ridgefield | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Sat., 9/23 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | PU:8:30 RE:11:30 | |
| Sat., 9/23 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 9:00 a.m. | PU:7:15 RE:10:30 | |
| Sat., 9/23 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 10:00 a.m. | PU:8:30 RE:11:30 | |
| Sat., 9/23 | V Girls Soccer | Trumbull | Home - Taft Field [Directions] | L 1-2 | ||
| Sat., 9/23 | JV Girls Soccer | Trumbull | Home - Sturges Park [Directions] | 1:00 p.m. | ||
| Sat., 9/23 | FR Girls Soccer | Trumbull | Away - The Pit [Directions] | 2:30 p.m. | PU:1:15 RE:4:00 | |
| Mon., 9/25 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | L 1 - 0 | PU:2:30 RE:6:30 | |
| Mon., 9/25 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 9/25 | FR Field Hockey | Darien | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Mon., 9/25 | V Girls Swimming and Diving | Greenwich | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/25 | V Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Mon., 9/25 | JV Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Wilton, Brien McMahon, Norwalk | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 9/26 | V Girls Cross Country | Wilton, Brien McMahon, Norwalk | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 9/26 | FR Girls Volleyball | Greenwich | Away - Western MS [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Wed., 9/27 | V Boys Soccer | Trinity Catholic | Home - Taft Field [Directions] | W 4-0 | ||
| Wed., 9/27 | FR Boys Soccer | Darien | Home - Roger Ludlowe MS [Directions] | 4:30 p.m. | ||
| Wed., 9/27 | V Field Hockey | Danbury | Home - Taft Field [Directions] | W 5 - 0 | ||
| Wed., 9/27 | JV Field Hockey | Danbury | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 9/27 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Wed., 9/27 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 5:30 p.m. | PU:3:30 RE:7:00 | |
| Wed., 9/27 | V Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Wed., 9/27 | JV Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/27 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Thu., 9/28 | FR Football | Greenwich | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 9/28 | V Girls Soccer | Trinity Catholic | Away - Gaglio Field | W 6-0 | PU:2:30 RE:5:30 | |
| Thu., 9/28 | FR Girls Volleyball | Trumbull | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Soccer | New Canaan | Away - Conner Field [Directions] | T 1-1 | PU:2:30 RE:5:30 | |
| Mon., 10/2 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Tue., 10/3 | V Boys Cross Country | Greenwich, Staples, Ridgefield | Away - Greenwich Point [Directions] | 4:30 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/3 | V Boys Soccer | New Canaan | Home - Taft Field [Directions] | W 2-1 | ||
| Tue., 10/3 | JV Boys Soccer | New Canaan | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/3 | V Girls Cross Country | Greenwich, Staples, Ridgefield | Away - Greenwich Point [Directions] | 4:30 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/3 | FR Girls Soccer | New Canaan | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | PU:2:30 RE:6:30 | |
| Tue., 10/3 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 10/4 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | T 2-2 | PU:4:00 RE:8:30 | |
| Wed., 10/4 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 10/4 | FR Field Hockey | Ridgefield | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Soccer | Bridgeport Central | Home - Taft Field [Directions] | W 6-0 | ||
| Wed., 10/4 | V Girls Volleyball | Trinity Catholic | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/4 | JV Girls Volleyball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Football | Brien McMahon | Home - Taft Field [Directions] | L 13-32 | ||
| Thu., 10/5 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | T 0-0 | PU:2:45 RE:5:30 | |
| Thu., 10/5 | JV Boys Soccer | Bridgeport Central | Away - Seaside Park #10 [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Fri., 10/6 | V Girls Soccer | Darien | Home - Taft Field [Directions] | T 1-1 | ||
| Fri., 10/6 | JV Girls Soccer | Darien | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Girls Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 10/6 | V Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Fri., 10/6 | JV Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Sat., 10/7 | JV Football | Brien McMahon | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Sat., 10/7 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | W 7-0 | PU:1:30 RE:5:30 | |
| Sat., 10/7 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 3:00 p.m. | Ride with Varsity | |
| Sat., 10/7 | V Girls Swimming and Diving | St. Joseph | Away - Orange Recreation Center [Directions] | 3:00 p.m. | PU:1:30 RE:4:30 | |
| Mon., 10/9 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | W 4 - 0 | PU:2:30 RE:6:30 | |
| Mon., 10/9 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 10/9 | V Girls Soccer | Westhill | Home - Taft Field [Directions] | W 3-1 | ||
| Mon., 10/9 | V Girls Volleyball | Joel Barlow | Home - FLHS Main Gym [Directions] | L 1-3 | ||
| Mon., 10/9 | JV Girls Volleyball | Joel Barlow | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | New Canaan, Danbury, St. Joseph, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/10 | V Boys Soccer | Westhill | Away - Westhill Football Field [Directions] | W 4-0 | PU:2:30 RE:5:30 | |
| Tue., 10/10 | JV Boys Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Tue., 10/10 | FR Boys Soccer | Westhill | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | New Canaan, Danbury, St. Joseph, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 10/11 | FR Football | Westhill | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 10/11 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | T 0-0 | PU:2:30 RE:5:30 | |
| Wed., 10/11 | JV Girls Soccer | St. Joseph | Away [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 10/11 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | PU:2:45 RE:6:30 | |
| Wed., 10/11 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | Ride with Varsity | |
| Thu., 10/12 | V Boys Soccer | St. Joseph | Home - Taft Field [Directions] | W 4-0 | ||
| Thu., 10/12 | JV Boys Soccer | St. Joseph | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Field Hockey | Fairfield Warde | Home - Taft Field [Directions] | W 9-0 | ||
| Thu., 10/12 | JV Field Hockey | Fairfield Warde | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | FR Girls Volleyball | Darien | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Football | Trinity Catholic | Away - Gaglio Field | L 19-40 | PU:3:00 RE:8:00 (2 buses) | |
| Fri., 10/13 | V Competitive Cheerleading | Trinity Catholic | Away | 6:00 p.m. | PU:4:30 RE:8:00 | |
| Fri., 10/13 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | W 3-2 | PU:2:30 RE:6:30 | |
| Fri., 10/13 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Sat., 10/14 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | T 0-0 | PU:2:30 RE:5:30 | |
| Sat., 10/14 | JV Boys Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | Ride with Varsity | |
| Sat., 10/14 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | W 2-0 | PU:2:30 RE:6:30 | |
| Sat., 10/14 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Sat., 10/14 | FR Field Hockey | New Canaan | Home - FLHS Front Field [Directions] | 12:00 p.m. | ||
| Sat., 10/14 | V Girls Soccer | Staples | Home - Taft Field [Directions] | L 0-2 | ||
| Sat., 10/14 | FR Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 1:30 p.m. | PU:12:30 RE:3:00 | |
| Sat., 10/14 | V Girls Volleyball | RI Invitational Tournament | Away - CCRI Lincoln, RI | 9:00 a.m. | ||
| Mon., 10/16 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | T 0-0 | PU:2:30 RE:5:30 | |
| Mon., 10/16 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 10/16 | FR Boys Soccer | Staples | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | JV Girls Soccer | Staples | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 1-3 | PU:2:30 RE:6:30 | |
| Mon., 10/16 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 10/16 | FR Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | JV Boys Soccer | Fairfield Warde | Home - Roger Ludlowe MS [Directions] | 3:30 p.m. | ||
| Tue., 10/17 | V Field Hockey | Westhill | Home - Taft Field [Directions] | W 9 - 1 | ||
| Tue., 10/17 | JV Field Hockey | Westhill | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | JV Girls Soccer | Fairfield Warde | Home - Sturges Park [Directions] | 3:30 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | PU:12:30 RE:5:30 | |
| Wed., 10/18 | V Boys Soccer | Fairfield Warde | Home - Taft Field [Directions] | W 1-0 | ||
| Wed., 10/18 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 3:30 p.m. | PU:2:30 No Return | |
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | PU:12:30 RE:5:30 | |
| Wed., 10/18 | V Girls Soccer | Fairfield Warde | Home - Taft Field [Directions] | T 1-1 | ||
| Wed., 10/18 | FR Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 3:30 p.m. | PU:2:30 No Return | |
| Wed., 10/18 | V Girls Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | L 2-3 | ||
| Wed., 10/18 | JV Girls Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Thu., 10/19 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Thu., 10/19 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | W 4 - 0 | PU:2:30 RE:6:30 | |
| Thu., 10/19 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | Ride with Varsity | |
| Thu., 10/19 | FR Field Hockey | Trumbull | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Girls Soccer | Wilton | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Boys Soccer | Norwalk | Home - RLMS [Directions] | W 3-1 | ||
| Fri., 10/20 | JV Boys Soccer | Norwalk | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | FR Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 10/20 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | PU:1:30 RE:4:30 | |
| Fri., 10/20 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 1-3 | PU:2:30 RE:6:30 | |
| Fri., 10/20 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Fri., 10/20 | FR Girls Volleyball | Staples | Away - Staples Field House [Directions] | 4:00 p.m. | ||
| Sat., 10/21 | V Field Hockey | Watertown | Home - Taft Field [Directions] | W 5 - 0 | ||
| Sat., 10/21 | JV Field Hockey | Watertown | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 2-0 | PU:11:15 RE:4:00 | |
| Sat., 10/21 | JV Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 2:30 p.m. | Ride with Varsity | |
| Mon., 10/23 | V Boys Soccer | Wilton | Home - Taft Field [Directions] | T 1-1 | ||
| Mon., 10/23 | JV Boys Soccer | Wilton | Home - Roger Ludlowe MS [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/23 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-1 | PU:5:45 RE:8:30 | |
| Mon., 10/23 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | PU:2:30 RE:6:30 | |
| Mon., 10/23 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:30 p.m. | Ride with JV | |
| Wed., 10/25 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 0-2 | PU:4:00 RE:8:30 | |
| Wed., 10/25 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 10/25 | FR Field Hockey | Norwalk | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | L 0-3 | PU:2:30 RE:5:30 | |
| Wed., 10/25 | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 10/25 | V Girls Volleyball | Norwalk | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/25 | JV Girls Volleyball | Norwalk | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Stamford | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Thu., 10/26 | V Girls Swimming and Diving | Fairfield Warde | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | V Football | Greenwich | Home - Taft Field [Directions] | L 20-42 | ||
| Fri., 10/27 | V Girls Volleyball | Wilton | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Fri., 10/27 | JV Girls Volleyball | Wilton | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 1:35 p.m. | PU:10:00 RE:2:15 | |
| Sat., 10/28 | JV Football | Greenwich | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 1:00 p.m. | Ride with Boys | |
| Wed., 11/1 | V Girls Swimming and Diving | FCIAC Swimming Trials | Away - Greenwich | 4:00 p.m. | PU:1:30 RE:6:00 | |
| Thu., 11/2 | FR Football | Ridgefield | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 11/2 | V Girls Swimming and Diving | Diving Finals | Away - Westhill | 4:30 p.m. | TBA | |
| Fri., 11/3 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | TBA | |
| Fri., 11/3 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 29-28 | PU:4:00 RE:9:00 (2 buses) | |
| Fri., 11/3 | V Competitive Cheerleading | Danbury | Away [Directions] | 7:00 p.m. | PU:5:30 RE:9:00 | |
| Fri., 11/3 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | PU:10:45 RE:3:15 | |
| Sat., 11/4 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 2:00 p.m. | PU:12:00 RE:3:30 | |
| Sat., 11/4 | V Girls Swimming and Diving | FCIAC Finals | Away | 6:00 p.m. | TBA | |
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | TBA | |
| Thu., 11/9 | FR Football | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 11/10 | V Football | New Canaan | Away - Dunning Stadium [Directions] | L 0-45 | PU:4:15 RE:9:00 (2 buses) | |
| Fri., 11/10 | V Competitive Cheerleading | New Canaan | Away [Directions] | 7:00 p.m. | PU:5:30 RE:9:00 | |
| Sat., 11/11 | V Boys Cross Country | New England Championship | Away - Troy Howard MS (Belfast, ME) [Directions] | TBA | TBA | |
| Sat., 11/11 | V Girls Cross Country | New England Championship | Away - Troy Howard MS (Belfast, ME) [Directions] | TBA | TBA | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | TBA | |
| Mon., 11/13 | JV Football | Fairfield Warde | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan [Directions] | 7:00 p.m. | TBA | |
| Wed., 11/15 | FR Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:00 p.m. | PU:3:30 RE:6:30 | |
| Thu., 11/16 | V Football | Bridgeport Central | Home - Taft Field [Directions] | L 44-46 | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | TBA | |
| Sat., 11/18 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 5:00 p.m. | TBA | |
| Thu., 11/23 | V Football | Fairfield Warde | Home - Taft Field [Directions] | L 22-55 | ||
| Sat., 12/2 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | 10:30 a.m. | ||
| Sat., 12/2 | V Girls Ice Hockey | FICAC Jamboree | Away | TBA | ||
| Mon., 12/4 | V Girls Basketball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:45 p.m. | PU:2:30 RE:5:15 | |
| Wed., 12/6 | V Girls Basketball | Bethel (Scrim.) | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/6 | V Girls Ice Hockey | West Haven/SHA (Scrim.) | Home - Wonderland of Ice [Directions] | 7:10 p.m. | ||
| Sat., 12/9 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - FLHS Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 12/11 | V Girls Basketball | Harding | Home - FLHS Main Gym [Directions] | W 60-21 | ||
| Mon., 12/11 | JV Girls Basketball | Harding | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/11 | FR Girls Basketball | Masuk | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/12 | V Bowling | Kolbe Cathedral | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Wed., 12/13 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:00 p.m. | PU:3:30 RE:6:30 | |
| Wed., 12/13 | V Boys Ice Hockey | Greenwich (Scrim.) | Home - Wonderland Of Ice [Directions] | 4:40 p.m. | ||
| Wed., 12/13 | V Wrestling | Wilton | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/15 | FR Girls Basketball | Fairfield Warde | Away - Warde Main gym [Directions] | 3:15 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Bassick | Home - FLHS Main Gym [Directions] | L 39-72 | ||
| Sat., 12/16 | JV Boys Basketball | Bassick | Home - FLHS Aux Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Bassick | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Notre Dame-Fairfield (Scrim.) | Home - Wonderland Of Ice [Directions] | 7:30 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Staples Developmental meet | Away - Staples Field House | 10:00 a.m. | PU:9:00 RE:2:00 | |
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 44-48 | PU:11:00 RE:2:00 | |
| Sat., 12/16 | V Girls Indoor Track | Staples Developmental meet | Away - Staples Field House | 10:00 a.m. | PU:9:00 RE:NO | |
| Mon., 12/18 | V Girls Ice Hockey | Greenwich | Home - Wonderland of Ice [Directions] | L 5-0 | ||
| Tue., 12/19 | V Bowling | Position Round | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | L 36-54 | PU:4:00 RE:8:30 | |
| Tue., 12/19 | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | Ride with Varsity | |
| Tue., 12/19 | FR Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 3:45 p.m. | PU:2:30 RE:5:15 | |
| Wed., 12/20 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | L 44-47 | PU:2:30 RE:7:00 | |
| Wed., 12/20 | JV Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 12/20 | FR Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/20 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | Final Score: 90 (H) - 83 (V) | PUFW:2:00 PUFL:2:15 RE:5:00 | |
| Wed., 12/20 | V Wrestling | Trumbull | Home - FLHS Aux Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/21 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Wonderland of Ice [Directions] | W 7-4 | ||
| Fri., 12/22 | V Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | L 38-53 | ||
| Fri., 12/22 | JV Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | 3:15 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | 2:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | L 33-38 | PU:1:45 RE:6:30 | |
| Fri., 12/22 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | 3:15 p.m. | Ride with Varsity | |
| Fri., 12/22 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 2:00 p.m. | PU:12:30 RE:3:30 | |
| Sat., 12/23 | V Boys Ice Hockey | West Haven Coop | Away - Bennett Rink [Directions] | W 7-4 | PU at WOI 11:30, RE 2:30 | |
| Sat., 12/23 | V Wrestling | Bristol Eastern Multi-Dual | Away | 9:00 a.m. | PU:6:30 RE:2:30 | |
| Wed., 12/27 | V Boys Basketball | Notre Dame-Fairfield | Away - Fairfield University [Directions] | L 31-64 | ||
| Wed., 12/27 | JV Boys Basketball | Notre Dame-Fairfield | Home - FLHS Main Gym [Directions] | 10:00 a.m. | ||
| Wed., 12/27 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | L 2-4 | PU at WOI 2:30, RE 5:30 | |
| Wed., 12/27 | V Girls Basketball | Staples | Home - Fairfield Warde Main Gym [Directions] | L 45-51 | ||
| Wed., 12/27 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 10:30 a.m. | ||
| Thu., 12/28 | V Boys Basketball | Fairfield Warde | Away - Fairfield Prep [Directions] | L 50-65 | ||
| Thu., 12/28 | JV Boys Basketball | Holiday Tournament | Home [Directions] | TBA | ||
| Thu., 12/28 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Wonderland Of Ice [Directions] | L 1-4 | ||
| Thu., 12/28 | V Wrestling | Brien McMahon, Stamford, Westhill | Away - Brien McMahon HS [Directions] | 10:00 a.m. | PU:8:30 RE:1:30 | |
| Thu., 12/28 | V Girls Basketball | St. Paul Catholic | Home [Directions] | L 49-52 | ||
| Fri., 12/29 | V Boys Indoor Track | Marine Corps Holiday Classic | Away - Armory | TBA | ||
| Fri., 12/29 | V Girls Indoor Track | Marine Corps Holiday Classic | Away - Armory | TBA | ||
| Tue., 1/2 | V Bowling | Greenwich | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 48-50 | PU:3:30 RE:8:30 | |
| Wed., 1/3 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | Ride with Varsity | |
| Wed., 1/3 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 1/3 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | Final Score: 97 (H) - 75 (V) | PUFW:1:35 PUFL:1:50 RE:4:30 | |
| Wed., 1/3 | V Wrestling | Nonnewaug | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | W 44-23 | ||
| Wed., 1/3 | JV Girls Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/4 | V Co-ed Alpine Skiing | Staples | Away - Mt. Southington [Directions] | 3:00 p.m. | PU FLHS 1:40, PU FWHS 1:50, RE 6:30 | Cheshire and Amity as well |
| Fri., 1/5 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 3-1 | PU:5:15FLHS RE:8:20 | |
| Sat., 1/6 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 54-70 | PU:11:45 RE:3:30 | |
| Sat., 1/6 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 12:30 p.m. | Ride with Freshmen | |
| Sat., 1/6 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 11:00 a.m.. | PU:9:30 RE:12:30 | |
| Sat., 1/6 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | W 4-3(OT) | ||
| Sat., 1/6 | V Boys Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:2:00 | |
| Sat., 1/6 | V Boys Indoor Track | Elm City Relays | Away - Floyd Little Athletic Center | TBA | TBA | |
| Sat., 1/6 | V Wrestling | Fairfield Warde Invitational | Away | 9:30 a.m. | PU:7:15 RE:NO | |
| Sat., 1/6 | V Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | L 33-45 | ||
| Sat., 1/6 | JV Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/6 | FR Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Away - Pomperaug HS | 1st of 12 | PU:8:00 RE:1:30 | |
| Sat., 1/6 | V Girls Ice Hockey | Avon | Home - Wonderland of Ice [Directions] | W 5-2 | ||
| Sat., 1/6 | V Girls Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:2:30 RE:NO | |
| Sat., 1/6 | V Girls Indoor Track | Elm City Relays | Away - Floyd Little Athletic Center | TBA | Ride with Boys | |
| Tue., 1/9 | V Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | L 27-39 | ||
| Tue., 1/9 | JV Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Bowling | Stratford | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | W 58-40 | PU:3:45 RE:8:30 | |
| Tue., 1/9 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | Ride with Varsity | |
| Tue., 1/9 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 1/10 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | W 6-1 | PU at WOI 5:30, RE 9:000 | at Wesleyan |
| Wed., 1/10 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | Final Score: 93 (H) - 82 (V) | PUFL:2:20 PUFW:2:35 RE:5:30 | |
| Wed., 1/10 | V Wrestling | Fairfield Warde | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | V Co-ed Alpine Skiing | Ridgefield | Away - Mt. Southington [Directions] | 3:00 p.m. | PU FLHS 1:40, PU FWHS 1:50, RE 6:30 | Weston, Farmington, Glastonbury as well |
| Thu., 1/11 | JV Wrestling | Fairfield Warde | Away [Directions] | 3:30 p.m. | PU:3:00 RE:NO | |
| Thu., 1/11 | V Girls Ice Hockey | Darien | Home - Wonderland of Ice [Directions] | L 0-4 | ||
| Fri., 1/12 | V Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | L 43-44 | ||
| Fri., 1/12 | JV Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Boys Ice Hockey | Trinity Catholic | Home - Wonderland Of Ice [Directions] | W 8-5 | ||
| Fri., 1/12 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 26-49 | PU:3:30 RE:8:30 | |
| Fri., 1/12 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | Ride with Varsity | |
| Fri., 1/12 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | PU:2:30 NO Return | |
| Fri., 1/12 | V Girls Gymnastics | Wilton | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe - 133.40 Wilton- 127.65 | ||
| Sat., 1/13 | V Boys Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:2:00 | |
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center | 3:00 p.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Molloy Stanner Games | Away - Armory | Cancelled | ||
| Sat., 1/13 | V Wrestling | Daniel Hand Duals | Away | 9:00 a.m. | PU:6:45 RE:2:30 | |
| Sat., 1/13 | V Co-ed Fencing | North Haven | Home - Fairfield Ludlowe H.S. [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | SCC Coaches Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:NO | |
| Sat., 1/13 | V Girls Indoor Track | Molloy Stanner Games | Away - Armory | Cancelled | ||
| Sun., 1/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 10-5 | PU:11:00 FLHS RE:2:15 | |
| Mon., 1/15 | V Boys Basketball | Bridgeport Central | Away - Webster Bank Arena [Directions] | L 51-61 | PU:9:30 RE:1:00 | |
| Mon., 1/15 | V Girls Gymnastics | Fairfield Warde, Trumbull, Pomperaug, Nonnewaug | Home - Gymnastics & Cheer Academy [Directions] | Trumbull- 140.00 Ludlowe- 135.55 Pomperaug- 126.90 Warde- 122.80 Nonnewaug- 107.95 | ||
| Tue., 1/16 | V Bowling | St. Joseph | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 1/16 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | L 1-0 | PU:2:10FWHS 2:25FLHS RE:5:45 | |
| Wed., 1/17 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | W 57-52 | PU:3:45 RE:8:30 | |
| Wed., 1/17 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | Cancelled | Ride with Varsity | |
| Wed., 1/17 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | Cancelled | PU:2:30 RE:5:30 | |
| Wed., 1/17 | V Wrestling | Darien | Away - DHS - South Gym [Directions] | 5:00 p.m. | PU:3:15 RE:5:45 | |
| Wed., 1/17 | V Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | L 25-32 | ||
| Wed., 1/17 | JV Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | Cancelled | ||
| Wed., 1/17 | FR Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | Cancelled | ||
| Thu., 1/18 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | Final Score: 94 (H) - 72 (V) | PU:FL:2:20 PUFW:2:35 RE:5:30 | |
| Fri., 1/19 | V Boys Indoor Track | Yale High School Classic | Away - Coxe Cage | TBA | PU:12:00 RE:5:30 | |
| Fri., 1/19 | V Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | W 43-39 | PU:2:30 RE:7:00 | |
| Fri., 1/19 | JV Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Fri., 1/19 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 1/19 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | W 8-5 | PU:6:30 RE:10:00 | |
| Fri., 1/19 | V Girls Indoor Track | Yale High School Classic | Away - Coxe Cage | TBA | ||
| Sat., 1/20 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 6-5(OT) | PU at WOI 5:00, RE 8:30 | |
| Sat., 1/20 | V Boys Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:2:00 | |
| Sat., 1/20 | V Boys Indoor Track | Yale High School Classic | Away - Coxe Cage | TBA | ||
| Sat., 1/20 | V Wrestling | New Milford Invitational | Away | 8:00 a.m. | PU:6:00 RE:6:00 | |
| Sat., 1/20 | V Co-ed Fencing | Hopkins School | Away | 10:00 a.m. | PU 7:30, RE 2:00 | |
| Sat., 1/20 | V Girls Gymnastics | Foran | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 135.60 Foran- 126.80 | ||
| Sat., 1/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | W 2-1 | PU:12:30FLHS RE:3:45 | |
| Sat., 1/20 | V Girls Indoor Track | Wilton Developmental Meet | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:NO | |
| Sat., 1/20 | V Girls Indoor Track | Yale High School Classic | Away - Coxe Cage | TBA | ||
| Mon., 1/22 | V Girls Gymnastics | Greenwich, Fairfield Warde | Home - Gymnastics & Cheer Academy [Directions] | Greenwich- 141.90 Ludlowe- 132.90 | ||
| Tue., 1/23 | V Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | L 37-50 | ||
| Tue., 1/23 | JV Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Bowling | Position Round | Home [Directions] | 3:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | W 65-47 | PU:2:30 RE:7:00 | |
| Tue., 1/23 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | Ride with Varsity | |
| Tue., 1/23 | FR Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | PU:2:30 RE:5:15 | |
| Tue., 1/23 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 5-2 | PU:3:00FLHS RE:6:30 | |
| Wed., 1/24 | V Boys Ice Hockey | Ridgefield | Home - Wonderland Of Ice [Directions] | L 1-8 | ||
| Wed., 1/24 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | PU:5:00 RE:8:15 | |
| Wed., 1/24 | V Co-ed Alpine Skiing | Westhill | Away - Mt. Southington [Directions] | 3:00 p.m. | PU FLHS 1:40, PU FWHS 1:50, RE 6:30 | Litchfield, Barlow, Fairfield Prep, Greenwich, St. Lukes as well |
| Thu., 1/25 | V Girls Ice Hockey | Suffield Coop | Home - Wonderland of Ice [Directions] | L 4-1 | ||
| Fri., 1/26 | V Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | L 26-35 | ||
| Fri., 1/26 | JV Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | Final Score: 104 (H) - 68 (V) | PUFW:1:30 PUFL:1:45 RE:4:30 | |
| Fri., 1/26 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 41-24 | PU:3:30 RE:8:30 | |
| Fri., 1/26 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | Ride with Varsity | |
| Fri., 1/26 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Sat., 1/27 | V Boys Ice Hockey | New Canaan | Home - Wonderland Of Ice [Directions] | W 3-1 | ||
| Sat., 1/27 | V Boys Indoor Track | Divisional Championship | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:1:00 | |
| Sat., 1/27 | V Wrestling | Joel Barlow, Pomperaug Coop, Harding/Bassick/Bridgeport Central | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Co-ed Fencing | Guilford Novice Tournament | Away | 9:00 a.m. | PU 7:30, RE 5:30 | |
| Sat., 1/27 | V Girls Indoor Track | Divisional Championship | Away - Wilton Field House | 9:30 a.m. | PU:8:00 RE:NO | |
| Sun., 1/28 | V Girls Gymnastics | Darien, Fairfield Warde | Away - Gymnastics & Cheer Academy, Fairfield [Directions] | Ludlowe- 133.00 Darien- 126.90 | ||
| Mon., 1/29 | V Boys Ice Hockey | South Windsor | Home - Wonderland Of Ice [Directions] | L 2-4 | ||
| Mon., 1/29 | V Co-ed Fencing | Guilford | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | set up is 5pm | |
| Tue., 1/30 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | PU:2:30 RE:6:45 | |
| Tue., 1/30 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | Ride with JV | |
| Tue., 1/30 | V Bowling | Bunnell | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | W 67-29 | ||
| Tue., 1/30 | JV Girls Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/30 | V Girls Gymnastics | Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | Hand- 133.50 Ludlowe- 131.50 | PU:2:30 RE:6:30 | |
| Wed., 1/31 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | L 6-9 | PU at WOI 6:30, RE 9:30 | |
| Wed., 1/31 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | Final Score: 95 (H) - 76 (V) | PUFW:1:30 PUFL:1:45 RE:4:45 | |
| Wed., 1/31 | V Wrestling | Norwalk | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Co-ed Alpine Skiing | Wilton | Away - Mt. Southington [Directions] | 3:00 p.m. | PU FLHS 1:40, PU FWHS 1:50, RE 6:30 | Cheshire Academy, Pomperaug, gilbert, Brunsiwck, and Hopkins as well |
| Wed., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 7-0 | PU:4:00 FLHS RE:7:15 | |
| Thu., 2/1 | JV Boys Ice Hockey | Trumbull | Away [Directions] | 4:00 p.m. | PU at WOI 3:00, RE 5:30 | at Shelton |
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championship | Away - Hillhouse | 4:30 p.m. | PU:2:30 RE:8:00 | |
| Thu., 2/1 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | Final Score: 93 (H) - 58 (V) | PU:FW:1:30 PUFL:1:45 RE:4:45 | |
| Thu., 2/1 | V Girls Basketball | Darien | Home - FLHS Main Gym [Directions] | W 46-34 | ||
| Thu., 2/1 | JV Girls Basketball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/1 | V Girls Ice Hockey | New Canaan | Home - Wonderland of Ice [Directions] | L 3-0 | ||
| Thu., 2/1 | V Girls Indoor Track | FCIAC Championship | Away - Hillhouse | 4:30 p.m. | PU:2:30 RE:NO | |
| Fri., 2/2 | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 6:15 p.m. | PU at WOI 5:00, RE 7:45 | |
| Fri., 2/2 | V Wrestling | Masuk, Newington, Manchester | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Girls Gymnastics | Westhill, New Canaan | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 134.95 Westhill- 110.40 New Canaan- 108.8 | ||
| Sat., 2/3 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | L 42-55 | PU:11:15 RE:2:30 | |
| Sat., 2/3 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 11:30 a.m. | Ride with Freshmen | |
| Sat., 2/3 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 10:00 a.m. | PU:8:45 RE:11:30 | |
| Sat., 2/3 | JV Wrestling | Ludlowe JV Tournament | Home - FLHS Main Gym [Directions] | 9:30 a.m. | ||
| Mon., 2/5 | JV Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 3:45 p.m. | PU at WOI 2:45, RE 5:15 | at Shelton |
| Mon., 2/5 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Wonderland of Ice [Directions] | W 8-4 | ||
| Tue., 2/6 | V Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | W 54-48(OT) | PU:3:30 RE:8:30 | |
| Tue., 2/6 | JV Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 5:15 p.m. | Ride with Varsity | |
| Tue., 2/6 | FR Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 2/6 | V Wrestling | Ridgefield | Away - RHS Aux Gym [Directions] | 7:00 p.m. | PU:5:15 RE:8:15 | |
| Tue., 2/6 | V Bowling | Platt | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Westhill | Home - FLHS Main Gym [Directions] | W 60-33 | ||
| Tue., 2/6 | JV Girls Basketball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Girls Gymnastics | Staples | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe-131.65 Staples-121.35 | ||
| Thu., 2/8 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | Final Score: 148 (H) - 34 (V) | PU:FW:2:20 PUFL:2:35 RE:6:00 | |
| Thu., 2/8 | V Co-ed Alpine Skiing | Danbury | Away - Mt. Southington [Directions] | 3:00 p.m. | PU FLHS 1:40, PU FWHS 1:50, RE 6:30 | Guilford, Darien, Daniel Hand, Laurelton Hall, New Canaan, and Southington as well |
| Thu., 2/8 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 9-0 | PU:5:30FLHS RE:8:45 | |
| Fri., 2/9 | V Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | L 39-40 | ||
| Fri., 2/9 | JV Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | V Boys Ice Hockey | St. Joseph | Home - Wonderland Of Ice [Directions] | W 5-3 | ||
| Fri., 2/9 | V Wrestling | FCIAC Tournament | Away - New Canaan | 4:30 p.m. | PU:2:30 RE:9:00 | |
| Fri., 2/9 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | W 62-51 | PU:3:45 RE:8:30 | |
| Fri., 2/9 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | Ride with Varsity | |
| Fri., 2/9 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Sat., 2/10 | V Boys Ice Hockey | Norwalk | Home - Wonderland Of Ice [Directions] | W 6-2 | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | TBA | |
| Sat., 2/10 | V Wrestling | FCIAC Finals | Away - New Canaan | 10:00 a.m. | PU:8:30 RE:NO | |
| Sat., 2/10 | V Co-ed Fencing | North Haven JV Tournament | Away | 9:00 a.m. | PU 7:30, RE 3:30 | |
| Sat., 2/10 | V Girls Gymnastics | FCIAC Championships | Away - Jonathan Law HS | 3rd of 9. 136.60 | TBA | |
| Sat., 2/10 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | TBA | |
| Mon., 2/12 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 51-64 | PU:3:45 RE:8:30 | |
| Mon., 2/12 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | Ride with Varsity | |
| Mon., 2/12 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 2/12 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-4 | PU at WOI 4:30, RE 7:30 | |
| Mon., 2/12 | V Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | L 53-54(OT) | ||
| Mon., 2/12 | JV Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/12 | FR Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/13 | FR Boys Basketball | Fairfield Warde | Home [Directions] | 5:00 p.m. | ||
| Tue., 2/13 | V Bowling | Joel Barlow | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 2/13 | FR Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 2/14 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 73-80 | PU:3:45 RE:8:45 | |
| Wed., 2/14 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 5:00 p.m. | Ride with Varsity | |
| Wed., 2/14 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | Final Score: 94 (H) - 75 (V) | PU:FW:2:30 PUFL:2:45 RE:5:30 | |
| Wed., 2/14 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 38-41 | PU:2:30 RE:7:00 | |
| Wed., 2/14 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 2/14 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | W 3-1 | PU:1:45FWHS 2:00FLHS RE:5:15 | |
| Thu., 2/15 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 3-8 | PU at WOI 3:30, RE 7:00 | |
| Fri., 2/16 | V Wrestling | Class L Sate Tournament | Away - Bristol Central | 4:00 p.m. | TBA | |
| Fri., 2/16 | V Girls Gymnastics | Oxford, Newtown, Pomperaug, Nonnewaug | Away - Auxiliary Gym [Directions] | Ludlowe-135.45 Newtown- 130.80 Oxford- 130.45 | PU:4:15 RE:7:30 | |
| Fri., 2/16 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Wonderland of Ice [Directions] | L 3-2 | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | TBA | |
| Sat., 2/17 | V Wrestling | Class L State Finals | Away - Bristol Central | 9:00 a.m. | TBA | |
| Sat., 2/17 | V Co-ed Fencing | Hopkins School | Away | 9:00 a.m. | PU 7:30, RE 2:00 | |
| Sat., 2/17 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | TBA | |
| Sun., 2/18 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | W 10-4 | PU at WOI 3:30, RE 6:30 | |
| Sun., 2/18 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | T 2-2 | PU:4:45FLHS RE:7:45 | |
| Mon., 2/19 | V Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | L 52-61 | ||
| Mon., 2/19 | JV Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 7-4 | PU at WOI 12:00, RE 3:30 | |
| Mon., 2/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Wonderland of Ice [Directions] | L 2-0 | ||
| Wed., 2/21 | V Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | L 45-67 | ||
| Wed., 2/21 | JV Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Westhill/Stamford | Home - Wonderland Of Ice [Directions] | W 5-0 | ||
| Wed., 2/21 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | Final Score: 37 (H) - 95 (V) | PUFL:3:15 PUFW:3:30 RE:7:00 | |
| Fri., 2/23 | JV Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 4:00 p.m. | PU at WOI 3:00, RE 5:30 | at Shelton |
| Fri., 2/23 | V Wrestling | CIAC State Open | Away - Hillhouse | 4:00 p.m. | TBA | |
| Sat., 2/24 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | L 1-7 | PU at WOI 11:00, bus stays with the team for the day | |
| Sat., 2/24 | V Boys Ice Hockey | Staples | Away [Directions] | 6:30 p.m. | at Darien | |
| Sat., 2/24 | V Wrestling | CIAC State Open Finals | Away - Hillhouse | 9:00 a.m. | TBA | |
| Mon., 2/26 | V Boys Ice Hockey | Amity | Home - Wonderland Of Ice [Directions] | L 4-5 | ||
| Mon., 2/26 | V Co-ed Fencing | Greenwich | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | set up at 5pm | |
| Mon., 2/26 | V Girls Basketball | Enfield | Away [Directions] | L 51-65 | ||
| Tue., 2/27 | V Bowling | Position Round | Home [Directions] | 3:00 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Greenwich | Away [Directions] | 4:50 p.m. | at Darien Ice House | |
| Thu., 3/1 | V Bowling | CIBL Team Tournament | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Fri., 3/2 | V Wrestling | New England Tournament | Away - Providence RI | 4:00 p.m. | TBA | |
| Sat., 3/3 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Sat., 3/3 | V Wrestling | New England Finals | Away - Providence RI | 9:00 a.m. | TBA | |
| Sat., 3/3 | V Bowling | State Championship | Away | 11:00 a.m. | PU 8:15, RE 2:00 | at Bowl-a-Rama in Newington |
| Sat., 3/3 | V Co-ed Fencing | State Tournament at Hopkins | Away | 9:00 a.m. | PU 7:00, RE 3:30 | |
| Sat., 3/3 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Mon., 3/5 | V Co-ed Fencing | State Championship at Hopkins | Away | 5:00 p.m. | PU 3:30, RE 7:00 | |
| Tue., 3/6 | V Bowling | CIBL Singles Tournament | Home [Directions] | 3:00 p.m. | ||
| Wed., 3/7 | V Boys Ice Hockey | Ridgefield | Away [Directions] | 7:30 p.m. | PU WOI 5:30, RE 9:00 | CIAC Division I first round |
| Fri., 3/9 | V Boys Ice Hockey | Ridgefield | Away [Directions] | 5:10 p.m. | PU WOI 3:00, RE 6:30 | |
| Sat., 3/10 | V Co-ed Fencing | East Lyme Team Tournament | Away | 9:00 a.m. | PU 6:30, RE 3:00 | |
| Tue., 3/20 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Testa Field, NHS [Directions] | 3:30 p.m. | PU:2:45 RE:5:30 | |
| Fri., 3/23 | V Boys Volleyball | Masuk (Scrim.) | Home [Directions] | 5:00 p.m. | ||
| Sat., 3/24 | V Baseball | Branford (Scrim.) | Away - James L. MacVeigh Alumni Athletic Complex - Baseball Field [Directions] | 10:30 a.m. | PU:9:00 RE:12:00 | |
| Sat., 3/24 | V Boys Lacrosse | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 12:00 p.m. | PU:11:00 RE:1:30 | 2 trips back and forth |
| Sat., 3/24 | V Girls Lacrosse | Cheshire (Scrim.) | Home - Taft Field [Directions] | 1:30 p.m. | ||
| Sat., 3/24 | JV Girls Lacrosse | Cheshire (Scrim.) | Home - Taft Field [Directions] | 2:45 p.m. | ||
| Mon., 3/26 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 3/26 | V Girls Lacrosse | Darien (Scrim.) | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Mon., 3/26 | V Softball | Bethel (Scrim.) | Home - Tom Hayden field [Directions] | 3:45 p.m. | ||
| Tue., 3/27 | V Baseball | Fairfield Warde (Scrim.) | Home - Kiwanis Field [Directions] | 3:30 p.m. | ||
| Tue., 3/27 | JV Baseball | Fairfield Warde (Scrim.) | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | Shuttle | |
| Tue., 3/27 | FR Baseball | Fairfield Warde (Scrim.) | Home - Owen Fish Park [Directions] | 4:00 p.m. | Shuttle | |
| Tue., 3/27 | V Boys Lacrosse | Trumbull (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 3/27 | JV Boys Lacrosse | Trumbull (Scrim.) | Home - Taft Field [Directions] | 6:30 p.m. | ||
| Wed., 3/28 | V Baseball | Fairfield Prep (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 3/28 | JV Baseball | Fairfield Prep (Scrim.) | Home - Owen Fish Park [Directions] | 4:00 p.m. | Shuttle | |
| Wed., 3/28 | V Boys Volleyball | Greenwich (Scrim.) | Away - GHS Gymnasium [Directions] | 4:00 p.m. | PU:3:00 RE:6:00 | |
| Wed., 3/28 | V Co-ed Sailing | Greenwich | Away [Directions] | 3:30 p.m. | PU:2:30 RE:5:15 | Also Vs. RHS & RCDS |
| Wed., 3/28 | V Softball | Brookfield (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 3/28 | JV Softball | Brookfield (Scrim.) | Home - Tom Haydon Field [Directions] | 4:15 p.m. | ||
| Thu., 3/29 | V Boys Lacrosse | Guilford (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 3/29 | V Softball | New Milford (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 3/29 | JV Softball | New Milford (Scrim.) | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Sat., 3/31 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Rafferty Stadium, Fairfield University [Directions] | 9:00 a.m. | ||
| Sat., 3/31 | V Girls Lacrosse | Greenwich | Home - Taft Field [Directions] | W 9-8 | ||
| Sat., 3/31 | JV Girls Lacrosse | Greenwich | Home - Taft Field [Directions] | 11:30 a.m. | ||
| Sat., 3/31 | V Softball | Amity (Scrim.) | Away [Directions] | 10:00 a.m. | PU:9:00 RE:1:30 | |
| Wed., 4/4 | V Boys Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Wed., 4/4 | JV Boys Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/4 | V Co-ed Sailing | Darien | Home [Directions] | 3:30 p.m. | Also Vs. SHS | |
| Wed., 4/4 | FR Girls Lacrosse | New Canaan | Home - Tomlinson MS [Directions] | 3:30 p.m. | ||
| Thu., 4/5 | V Baseball | Ridgefield | Home - Kiwanis Field [Directions] | L 6-4 | ||
| Thu., 4/5 | JV Baseball | Ridgefield | Home - Owen Fish Park [Directions] | 4:00 p.m. | Shuttle | |
| Thu., 4/5 | V Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | W 11-10 | ||
| Thu., 4/5 | V Boys Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | W 5-2 | PU:2:30 RE:5:30 | |
| Thu., 4/5 | V Girls Golf | Staples | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 204 Staples - 221 | ||
| Thu., 4/5 | V Girls Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | L 6-7 | ||
| Thu., 4/5 | V Softball | Sheehan | Away - Pragemann Park-Oak Street [Directions] | L 2-1 | PU:2:20 RE:5:30 | |
| Thu., 4/5 | JV Softball | Sheehan | Away - Pragemann Park-Oak Street [Directions] | 5:30 p.m. | Ride with Varsity | |
| Thu., 4/5 | V Girls Tennis | Danbury | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/6 | V Boys Outdoor Track | Bridgeport Central, Weston | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Fri., 4/6 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | PU:2:45 RE:6:30 | |
| Fri., 4/6 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Fri., 4/6 | FR Girls Lacrosse | Trumbull | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Fri., 4/6 | V Girls Outdoor Track | Bridgeport Central | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 4/7 | V Baseball | North Haven | Away - North Haven Athletic Complex-DeMayo Field [Directions] | L 13-3(6) | PU:12:15 RE:3:30 | |
| Sat., 4/7 | JV Baseball | North Haven | Home - Kiwanis Field [Directions] | 1:00 p.m. | ||
| Sat., 4/7 | FR Baseball | North Haven | Away - Bailey Road Field [Directions] | 2:00 p.m. | Ride with Varsity | |
| Sat., 4/7 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | PU:2:30 RE:5:30 | |
| Sat., 4/7 | V Co-ed Sailing | NESSA Super Saturday 1 | Away | TBA | ||
| Sat., 4/7 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | L 5-12 | PU:11:45 RE:4:30 | |
| Sat., 4/7 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 1:00 p.m. | Ride with Varsity | |
| Mon., 4/9 | V Baseball | Stamford | Home - Kiwanis Field [Directions] | L 8-7(8) | ||
| Mon., 4/9 | V Baseball | Stamford | Home - Kiwanis Field [Directions] | L 9-4 | ||
| Mon., 4/9 | JV Baseball | Stamford | Home - Tunxis Hill Park [Directions] | 11:00 a.m. | Shuttle | |
| Mon., 4/9 | JV Baseball | Stamford | Home - Tunxis Hill Park [Directions] | 1:30 p.m. | Shuttle | |
| Mon., 4/9 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 11:00 a.m. | ||
| Mon., 4/9 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 1:30 p.m. | PU:9:45 RE:3:00 | |
| Mon., 4/9 | V Boys Tennis | Greenwich | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Mon., 4/9 | V Softball | Stamford | Away - Stamford HS [Directions] | W 5-1 | PU:11:30 RE:3:30 | |
| Mon., 4/9 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 | PU:9:30 RE:12:30 | |
| Tue., 4/10 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 2-17 | PU:2:30 RE:5:30 | |
| Tue., 4/10 | JV Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Tue., 4/10 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 13-0 | PU:2:45 RE:7:00 | |
| Tue., 4/10 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | Ride with Varsity | |
| Wed., 4/11 | V Baseball | Brien McMahon | Away - Pride Field At BMHS [Directions] | W 7-5 | PU:9:30 RE:12:30 | |
| Wed., 4/11 | JV Baseball | Brien McMahon | Away - Pride Field (BMNS) [Directions] | 1:45 p.m. | PU:12:30 RE:3:15 | |
| Wed., 4/11 | V Softball | Brien McMahon | Home - Sturges Park [Directions] | W 20-8 | ||
| Thu., 4/12 | V Boys Lacrosse | Conard | Home - Taft Field [Directions] | W 12-8 | ||
| Thu., 4/12 | JV Boys Lacrosse | Conard | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 4/12 | V Girls Lacrosse | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | W 12-5 | PU:2:00 RE:6:30 | |
| Thu., 4/12 | JV Girls Lacrosse | Guilford | Away - Long Hill Park - Guilford [Directions] | 3:45 p.m. | Ride with Varsity | |
| Thu., 4/12 | V Softball | Staples | Away - Wakeman Field [Directions] | W 16-3 | PU:2:45 RE:5:30 | |
| Fri., 4/13 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | L 12-3 | PU:2:30 RE:5:30 | |
| Fri., 4/13 | JV Baseball | Danbury | Away - Westerner Baseball Field, Rogers Park [Directions] | 3:45 p.m. | Ride with Varsity | |
| Fri., 4/13 | FR Baseball | Danbury | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/13 | V Softball | Danbury | Home - Sturges Park [Directions] | W 5-4 | ||
| Sat., 4/14 | V Boys Lacrosse | Cheshire | Away - West Point, New York [Directions] | L 7-10 | TBA | |
| Sat., 4/14 | V Co-ed Sailing | NESSA Super Saturday 2 | Away | TBA | ||
| Mon., 4/16 | V Boys Volleyball | Stamford | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Mon., 4/16 | JV Boys Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/16 | FR Girls Lacrosse | Staples | Home - Tomlinson MS [Directions] | 3:30 p.m. | ||
| Tue., 4/17 | V Boys Golf | Westhill | Away - Hubbard Brennan Golf Course [Directions] | Ludlowe 166/Westhill 173 | PU:2:00 RE:5:15 | |
| Tue., 4/17 | V Boys Lacrosse | Kennedy Catholic-Somers (NY) | Away | W 16-8 | PU:2:30 RE:6:00 | |
| Tue., 4/17 | JV Boys Lacrosse | Kennedy Catholic-Somers (NY) | Away | 4:30 p.m. | Ride with Varsity | |
| Tue., 4/17 | V Boys Outdoor Track | Norwalk, New Canaan | Away - Testa Field, NHS [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 busses |
| Tue., 4/17 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 4-3 | PU:2:30 RE:5:30 | |
| Tue., 4/17 | JV Boys Tennis | Darien | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/17 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | L 0-3 | PU:3:00 RE:7:00 | |
| Tue., 4/17 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:30 p.m. | Ride with Varsity | |
| Tue., 4/17 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | W 16-2 | PU:2:30 RE:6:30 | |
| Tue., 4/17 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Tue., 4/17 | V Softball | Greenwich | Away - Bruce Park Field [Directions] | W 14-6 | PU:2:45 RE:6:00 | |
| Tue., 4/17 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | Ride with Varsity | |
| Tue., 4/17 | V Girls Tennis | Trumbull | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 5-2 | ||
| Tue., 4/17 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Tue., 4/17 | Miscellaneous Events | Middle School Track Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 4/18 | V Boys Golf | St. Joseph | Home - Smith Richardson Golf Course [Directions] | Ludlowe 174/St Joseph 189 | ||
| Wed., 4/18 | JV Boys Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 4/18 | V Boys Tennis | Fairfield Prep | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 2-5 | ||
| Wed., 4/18 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 1-3 | PU:3:00 RE:6:30 | |
| Wed., 4/18 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 4/18 | V Co-ed Sailing | Greenwich Academy | Away | 3:30 p.m. | PU:2:30 RE:5:15 | Also Vs. BS & SHS |
| Wed., 4/18 | V Girls Outdoor Track | New Canaan, Norwalk | Away - NCHS Track Field [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 busses |
| Wed., 4/18 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 16-4 | PU:2:30 RE:5:30 | |
| Wed., 4/18 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 3:30 p.m. | PU:2:30 RE:5:00 | |
| Thu., 4/19 | V Girls Lacrosse | New Canaan | Home - Taft Field [Directions] | L 6-12 | ||
| Thu., 4/19 | JV Girls Lacrosse | New Canaan | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Fri., 4/20 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Fri., 4/20 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 4/20 | FR Baseball | Trumbull | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Boys Lacrosse | Trinity Catholic | Away - Gaglio Field | W 16-0 | PU:2:20 RE:5:30 | |
| Fri., 4/20 | V Boys Tennis | Ridgefield | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | ||
| Fri., 4/20 | JV Boys Tennis | New Canaan | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Boys Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | W 3-2 | ||
| Fri., 4/20 | JV Boys Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/20 | V Softball | Trumbull | Home - Sturges Park [Directions] | L 4-1 | ||
| Fri., 4/20 | JV Softball | Trumbull | Home - Tom Haydon Field [Directions] | 4:15 p.m. | ||
| Fri., 4/20 | V Girls Tennis | Brien McMahon | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/20 | JV Girls Tennis | New Canaan | Home - Dwight Elementary School [Directions] | 4:00 p.m. | ||
| Sat., 4/21 | V Baseball | Greenwich | Home - Kiwanis Field [Directions] | L 4-9 | ||
| Sat., 4/21 | V Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | W 15-4(6) | PU:10:30 RE:1:30 | |
| Sat., 4/21 | FR Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 12:00 p.m. | PU:10:30 RE:1:30 | |
| Sat., 4/21 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 13-1 | PU:8:30 RE:11:30 | |
| Sat., 4/21 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 12:00 p.m. | PU:10:30 RE:1:30 | |
| Sat., 4/21 | V Boys Outdoor Track | Lawmen Froshmore Meet | Away - Jonathan Law HS | 10:00 a.m. | ||
| Sat., 4/21 | V Co-ed Sailing | NESSA O'Day Qualifiers | Away | TBA | Vs Greenwich & Newport | |
| Sat., 4/21 | V Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | W 19-0 | PU:8:30 RE:1:00 | |
| Sat., 4/21 | JV Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | 12:00 p.m. | Ride with Varsity | |
| Sat., 4/21 | V Girls Outdoor Track | Lawmen Froshmore Meet | Away - Jonathan Law HS | 10:00 a.m. | ||
| Sat., 4/21 | V Softball | Masuk | Home - Sturges Park [Directions] | L 0-1 | ||
| Mon., 4/23 | V Boys Golf | Greenwich | Away - Greenwich Country Club [Directions] | Ludlowe 185/Greenwich 161 | PU:2:00 RE:5:15 | |
| Mon., 4/23 | V Boys Tennis | Trinity Catholic | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/23 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-2 | PU:2:45 RE:6:30 | |
| Mon., 4/23 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 4/23 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Ludlowe - 189 Warde - 178 | ||
| Mon., 4/23 | V Girls Outdoor Track | Brien McMahon, St. Joseph | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Mon., 4/23 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | PU:2:30 RE:5:30 | |
| Tue., 4/24 | V Baseball | Trinity Catholic | Home - Kiwanis Field [Directions] | W 11-1(5) | ||
| Tue., 4/24 | JV Baseball | Greenwich | Home - Owen Fish Park [Directions] | 4:30 p.m. | Shuttle | |
| Tue., 4/24 | V Boys Golf | Staples | Away - Longshore [Directions] | Ludlowe 153/Staples 149 | PU:2:20 RE:5:15 | |
| Tue., 4/24 | V Boys Outdoor Track | Brien McMahon, St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 4/24 | V Boys Tennis | New Canaan | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/24 | JV Boys Tennis | New Canaan | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/24 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Ludlowe - 201 Greenwich - 203 | PU:2:30 RE:5:45 | |
| Tue., 4/24 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:45 p.m. | ||
| Tue., 4/24 | V Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | W 15-3 | ||
| Tue., 4/24 | JV Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 4/24 | V Softball | Harding | Home - Sturges Park [Directions] | W 25-0 | ||
| Tue., 4/24 | JV Softball | Harding | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Tue., 4/24 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 0-7 | PU:2:30 RE:5:30 | |
| Tue., 4/24 | JV Girls Tennis | New Canaan | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/25 | V Boys Golf | Trinity Catholic | Home - Smith Richardson Golf Course [Directions] | Ludlowe 157/Trinity Catholic 236 | ||
| Wed., 4/25 | V Boys Lacrosse | Stamford | Home - Taft Field [Directions] | W 14-5 | ||
| Wed., 4/25 | JV Boys Lacrosse | Stamford | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 4/25 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | PU:2:30 RE:6:30 | |
| Wed., 4/25 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Thu., 4/26 | V Baseball | Naugatuck | Away - Naugatuck HS [Directions] | W 12-10 | PU:2:30 RE:5:30 | |
| Thu., 4/26 | JV Baseball | Trinity Catholic | Home - Kiwanis Field [Directions] | 4:00 p.m. | Shuttle | |
| Thu., 4/26 | FR Baseball | Naugatuck | Away - Rotary Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Thu., 4/26 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | PU:2:45 RE:5:30 | |
| Thu., 4/26 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | Ludlowe - 168 Wilton - 195 | PU:2:10 RE:5:30 | |
| Thu., 4/26 | V Girls Lacrosse | Pomperaug | Home - Taft Field [Directions] | W 12-6 | ||
| Thu., 4/26 | JV Girls Lacrosse | Pomperaug | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 4/26 | FR Girls Lacrosse | Wilton | Home - FLHS Front Field [Directions] | 4:30 p.m. | ||
| Thu., 4/26 | V Girls Tennis | Bridgeport Central | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/26 | JV Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | Cancelled | PU:4:00 RE:6:30 | |
| Fri., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 5:00 p.m. | ||
| Fri., 4/27 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | PU:2:30 RE:5:30 | |
| Fri., 4/27 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | Cancelled | ||
| Fri., 4/27 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Fri., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 5:00 p.m. | ||
| Fri., 4/27 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | W 6-2 | PU:2:30 RE:5:30 | |
| Sat., 4/28 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 14-9 | PU:11:30 RE:2:30 | |
| Sat., 4/28 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 11:00 a.m. | PU:9:30 RE:12:30 | |
| Sat., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | TBA | ||
| Sat., 4/28 | V Co-ed Sailing | NESSA States | Away - Coast Guard Academy | TBA | PU:8:30 RE:5:00 | |
| Sat., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | TBA | ||
| Sun., 4/29 | V Co-ed Sailing | NESSA Herreshoff Qualifiers | Away | TBA | Vs. Hotckiss & Tabor | |
| Mon., 4/30 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | W 15-1 | PU:2:30 RE:5:30 | |
| Mon., 4/30 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 4/30 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | Ludlowe 171/ Wilton 180 | PU:2:10 RE:5:15 | |
| Mon., 4/30 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 0-7 | PU:2:30 RE:5:30 | |
| Mon., 4/30 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 4/30 | V Boys Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Mon., 4/30 | JV Boys Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/30 | V Girls Golf | Darien | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 185 Darien - 214 | ||
| Mon., 4/30 | V Girls Outdoor Track | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 busses |
| Mon., 4/30 | V Softball | Bridgeport Central | Home - Sturges Park [Directions] | W 14-0 | ||
| Mon., 4/30 | JV Softball | Bridgeport Central | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Mon., 4/30 | V Girls Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | ||
| Mon., 4/30 | JV Girls Tennis | Darien | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Baseball | New Canaan | Home - Kiwanis Field [Directions] | W 16-12 | ||
| Tue., 5/1 | JV Baseball | New Canaan | Home - Owen Fish Park [Directions] | 4:00 p.m. | Shuttle | |
| Tue., 5/1 | FR Baseball | Ridgefield | Away - Branchville Civic (Playground Field) [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 5/1 | JV Boys Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | L 5-16 | PU:2:30 RE:5:30 | |
| Tue., 5/1 | JV Boys Lacrosse | New Canaan | Away - WTT2 [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 5/1 | V Boys Outdoor Track | Trumbull | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Boys Tennis | Westhill | Away - Cummings Park [Directions] | L 3-4 | PU:3:00 RE:5:30 | |
| Tue., 5/1 | V Girls Golf | Danbury | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 187 Danbury - 233 | ||
| Tue., 5/1 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 11-12 | PU:4:15 RE:7:30 | |
| Tue., 5/1 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | PU:3:15 RE:5:30 | |
| Tue., 5/1 | FR Girls Lacrosse | Darien | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Girls Tennis | Westhill | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/1 | JV Girls Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 3:15 p.m. | PU:3:00 NO Return | |
| Wed., 5/2 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | L 3-4 | PU:2:30 RE:5:30 | |
| Wed., 5/2 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 5/2 | FR Baseball | Darien | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 5/2 | V Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | Ludlowe 162/ Brien McMahon 226 | PU:2:15 RE:5:15 | |
| Wed., 5/2 | JV Boys Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 5/2 | JV Boys Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:30 p.m. | ||
| Wed., 5/2 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 0-3 | PU:2:30 RE:6:30 | |
| Wed., 5/2 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 5/2 | V Co-ed Sailing | Greenwich | Away [Directions] | 3:30 p.m. | PU:2:30 RE:5:15 | Also Vs. Fairfield Prep & GFA |
| Wed., 5/2 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:45 p.m. | ||
| Wed., 5/2 | V Softball | Darien | Home - Sturges Park [Directions] | W 6-0 | ||
| Wed., 5/2 | JV Softball | Darien | Home - Tom Haydon Field [Directions] | Cancelled | ||
| Wed., 5/2 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 6-1 | PU:2:00 RE:5:00 | |
| Wed., 5/2 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| Thu., 5/3 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 5/3 | V Boys Golf | Danbury, Fairfield Warde | Away - Richter Park Golf Course [Directions] | Ludlowe 170/ Danbury 189 | PU:1:45 RE:5:15 | |
| Thu., 5/3 | V Boys Tennis | St. Joseph | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/3 | V Girls Golf | Ridgefield, Fairfield Warde | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Ludlowe - 186 Ridgefield - 186 | PU:2:15 RE:5:30 | |
| Thu., 5/3 | V Girls Lacrosse | Lauralton Hall | Home - Taft Field [Directions] | W 17-1 | ||
| Thu., 5/3 | JV Girls Lacrosse | Lauralton Hall | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 5/3 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | PU:3:00 RE:5:00 | |
| Thu., 5/3 | V Girls Tennis | St. Joseph | Away - St. Joseph HS [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Thu., 5/3 | JV Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | 3:30 p.m. | PU:2:30 RE:5:00 | |
| Fri., 5/4 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | W 19-7 (6) | PU:2:30 RE:5:30 | |
| Fri., 5/4 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 5/4 | FR Baseball | Westhill | Home - Kiwanis Field [Directions] | 4:30 p.m. | ||
| Fri., 5/4 | JV Boys Tennis | Fairfield Warde | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | V Boys Volleyball | Darien | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Fri., 5/4 | JV Boys Volleyball | Darien | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/4 | FR Girls Lacrosse | Norwalk | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | V Softball | Westhill | Home - Sturges Park [Directions] | W 12-0 | ||
| Fri., 5/4 | JV Softball | Westhill | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Sat., 5/5 | V Boys Lacrosse | Staples | Home - Taft Field [Directions] | W 10-6 | ||
| Sat., 5/5 | JV Boys Lacrosse | Staples | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Sat., 5/5 | V Girls Lacrosse | Morgan | Home - Taft Field [Directions] | W 17-3 | ||
| Sat., 5/5 | JV Girls Lacrosse | Morgan | Home - Taft Field [Directions] | 1:30 p.m. | ||
| Mon., 5/7 | V Baseball | St. Joseph | Home - Kiwanis Field [Directions] | L 9-7 (10) | ||
| Mon., 5/7 | JV Baseball | St. Joseph | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | Shuttle | |
| Mon., 5/7 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Mon., 5/7 | V Boys Golf | Norwalk | Home - Smith Richardson Golf Course [Directions] | Ludlowe 153/ Norwalk 209 | ||
| Mon., 5/7 | JV Boys Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 5/7 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 0-7 | PU:2:30 RE:5:30 | |
| Mon., 5/7 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 5/7 | V Boys Volleyball | Ridgefield | Away - Main Gym [Directions] | L 0-3 | PU:2:45 RE:7:00 | |
| Mon., 5/7 | JV Boys Volleyball | Ridgefield | Away - Main Gym [Directions] | 4:30 p.m. | Ride with Varsity | |
| Mon., 5/7 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Mon., 5/7 | V Girls Outdoor Track | Wilton, Darien | Away - WHS Track [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 busses |
| Mon., 5/7 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | W 4-3 | PU:2:45 RE:5:30 | |
| Mon., 5/7 | JV Softball | St. Joseph | Away - Long Hill Administration field, Trumbull CT [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 5/7 | V Girls Tennis | Staples | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Mon., 5/7 | JV Girls Tennis | Staples | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/8 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | Ludlowe 172/ Darien 151 | PU:2:15 RE:5:15 | |
| Tue., 5/8 | JV Boys Golf | Gene Mulak Classic | Away - Silver Springs, Ridgefield, CT | 4:00 p.m. | PU:3:00 RE:6:00 | |
| Tue., 5/8 | V Boys Lacrosse | St. Joseph | Home - Taft Field [Directions] | L 10-11(2OT) | ||
| Tue., 5/8 | JV Boys Lacrosse | St. Joseph | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 5/8 | V Boys Outdoor Track | Darien, Wilton | Away - DHS Track [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 busses |
| Tue., 5/8 | V Boys Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | W 6-1 | PU:2:45 RE:5:30 | |
| Tue., 5/8 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | Ride with Varsity | |
| Tue., 5/8 | V Girls Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 199 New Canaan - 183 | ||
| Tue., 5/8 | JV Girls Golf | New Canaan | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/8 | FR Girls Lacrosse | Fairfield Warde | Home - FLHS Front Field [Directions] | 3:45 p.m. | ||
| Tue., 5/8 | V Girls Tennis | Fairfield Warde | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/8 | JV Girls Tennis | Fairfield Warde | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | V Baseball | Staples | Away - Staples Baseball Field [Directions] | L 12-2(5) | PU:2:45 RE:5:30 | |
| Wed., 5/9 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 5/9 | FR Baseball | Staples | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | V Boys Golf | Trumbull, Fairfield Warde | Away - Tashua Knolls Golf Course [Directions] | Ludlowe 166/ Trumbull 162 | PU:2:15 RE:5:15 | |
| Wed., 5/9 | JV Boys Golf | Trumbull | Away - Tashua Knolls [Directions] | 3:15 p.m. | Ride with Varsity | |
| Wed., 5/9 | V Boys Volleyball | New Canaan | Home - FLHS Aux Gym [Directions] | L 1-3 | ||
| Wed., 5/9 | JV Boys Volleyball | New Canaan | Home - FLHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/9 | V Softball | Staples | Home - Sturges Park [Directions] | W 8-6 | ||
| Wed., 5/9 | JV Softball | Staples | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Wed., 5/9 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Wed., 5/9 | JV Girls Tennis | Weston | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Boys Lacrosse | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | W 15-8 | PU:4:15 RE:8:00 | |
| Thu., 5/10 | JV Boys Lacrosse | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 4:30 p.m. | PU:2:15 RE:6:00 | |
| Thu., 5/10 | V Boys Tennis | Norwalk | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/10 | JV Boys Tennis | Ridgefield | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Boys Volleyball | Fairfield Warde | Home - FLHS Aux Gym [Directions] | L 0-3 | ||
| Thu., 5/10 | JV Boys Volleyball | Fairfield Warde | Home - FLHS Aux Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/10 | V Girls Golf | Staples | Away - Longshore [Directions] | Ludlowe - 183 Staples - 195 | PU:2:00 RE:5:00 | |
| Thu., 5/10 | JV Girls Golf | Staples | Away - Longshore [Directions] | 3:30 p.m. | Ride with Varsity | |
| Thu., 5/10 | V Girls Lacrosse | St. Joseph | Home - Taft Field [Directions] | W 10-3 | ||
| Thu., 5/10 | JV Girls Lacrosse | St. Joseph | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 5/10 | FR Girls Lacrosse | Ridgefield | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Thu., 5/10 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Thu., 5/10 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 5/11 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 6-1 | ||
| Fri., 5/11 | V Boys Outdoor Track | Irv Black Invitational | Away - Willow Brook Park | 3:30 p.m. | ||
| Fri., 5/11 | V Girls Outdoor Track | Irv Black Invitational | Away - Willow Brook Park | 3:30 p.m. | ||
| Fri., 5/11 | V Softball | Fairfield Warde | Home - Dougiello Field [Directions] | W 5-4 | Shuttle | |
| Fri., 5/11 | JV Softball | Harding | Away - Luis Munoz Marin School [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Sat., 5/12 | V Boys Lacrosse | Wilton | Home - Taft Field [Directions] | L 9-16 | ||
| Sat., 5/12 | JV Boys Lacrosse | Wilton | Home - Taft Field [Directions] | 12:00 p.m. | ||
| Sat., 5/12 | V Boys Outdoor Track | Irv Black Invitational | Away - Willow Brook Park | 10:00 a.m. | PU:8:15 RE:2:00 | |
| Sat., 5/12 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 14-2 | PU:9:30 RE:2:00 | |
| Sat., 5/12 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 1:00 p.m. | Ride with Varsity | |
| Sat., 5/12 | V Girls Outdoor Track | Irv Black Invitational | Away - Willow Brook Park | 10:00 a.m. | Ride with Boys | |
| Mon., 5/14 | V Baseball | Norwalk | Home - Kiwanis Field [Directions] | L 3-4 | ||
| Mon., 5/14 | JV Baseball | Norwalk | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | Shuttle | |
| Mon., 5/14 | FR Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 5/14 | JV Boys Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/14 | V Boys Lacrosse | Weston | Home - Taft Field [Directions] | W 12-11 | ||
| Mon., 5/14 | JV Boys Lacrosse | Weston | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Mon., 5/14 | V Boys Tennis | Wilton | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 4-3 | ||
| Mon., 5/14 | JV Boys Tennis | Wilton | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-2 | PU:2:45 RE:6:30 | |
| Mon., 5/14 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 5/14 | V Girls Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 180 Wilton - 218 | ||
| Mon., 5/14 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 20-3 | PU:2:30 RE:6:30 | |
| Mon., 5/14 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 5/14 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | L 5-3 | PU:2:30 RE:5:30 | |
| Mon., 5/14 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 5/14 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 2-5 | PU:2:30 RE:5:30 | |
| Mon., 5/14 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | Ride with Varsity | |
| Tue., 5/15 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | PU:2:30 RE:6:00 | |
| Tue., 5/15 | V Boys Outdoor Track | Fairfield Warde | Home - Taft Field [Directions] | 3:00 p.m. | ||
| Tue., 5/15 | V Boys Tennis | Stamford | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/15 | V Girls Outdoor Track | Fairfield Warde | Home - Taft Field [Directions] | 3:00 p.m. | ||
| Tue., 5/15 | JV Girls Tennis | Ridgefield | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/16 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | PU:2:30 RE:6:30 | |
| Wed., 5/16 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | Ride with Varsity | |
| Wed., 5/16 | JV Girls Golf | Danbury, Darien | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Wed., 5/16 | Unified Sports Track | Track Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 5/17 | V Baseball | Wilton | Home - Nathan Hale MS Norwalk [Directions] | W 8-5 | ||
| Thu., 5/17 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Ludlowe 179/ New Canaan 163 | PU:2:10 RE:5:15 | |
| Thu., 5/17 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:15 p.m. | No Bus | |
| Thu., 5/17 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | PU:3:15 RE:6:30 | |
| Fri., 5/18 | FR Baseball | Fairfield Warde | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Fri., 5/18 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 5-15 | PU:4:30 RE:8:00 | |
| Fri., 5/18 | FR Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | 3:45 p.m. | PU:2:45 RE:5:00 | |
| Fri., 5/18 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | W 6-1 | PU:2:45 RE:5:45 | |
| Mon., 5/21 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | Shuttle | |
| Mon., 5/21 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 5/21 | V Boys Golf | Ridgefield | Home - Smith Richardson Golf Course [Directions] | Ludlowe 166/ Ridgefield 169 | ||
| Mon., 5/21 | JV Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 7:00 p.m. | PU:3:30 RE:NO | |
| Mon., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Southern CT State University | 1:30 p.m. | PU:11:30 RE:6:00 | |
| Mon., 5/21 | V Boys Volleyball | Kolbe Cathedral | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Mon., 5/21 | JV Boys Volleyball | Kolbe Cathedral | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/21 | V Girls Golf | Trumbull | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 186 Trumbull - 212 | ||
| Mon., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Southern CT State University | 1:30 p.m. | PU:11:30 RE:6:00 | |
| Tue., 5/22 | V Boys Golf | Stamford | Home - Smith Richardson Golf Course [Directions] | Ludlowe 153/Stamford 225 | ||
| Tue., 5/22 | V Girls Golf | Fairfield Warde, Ridgefield | Home - Smith Richardson Golf Course [Directions] | Ludlowe - 184 Warde - 172 Ridgefield - 200 | ||
| Wed., 5/23 | V Boys Golf | Fairfield Warde, Fairfield Prep | Away - Smith Richardson [Directions] | Ludlowe 170/ Warde 176 | No Bus | |
| Wed., 5/23 | V Girls Golf | St. Joseph | Away - Tashua Knolls, Trumbull [Directions] | Ludlowe - 176 St. Joe's - 267 | PU:2:20 RE:5:30 | |
| Wed., 5/23 | JV Girls Golf | JV Championship | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Wed., 5/23 | V Girls Lacrosse | Staples (Scrim.) | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Thu., 5/24 | V Girls Tennis | Pomperaug (Scrim.) | Home - Fairfield Ludlowe Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/29 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | ||
| Tue., 5/29 | Miscellaneous Events | Unified Track Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 5/30 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Mon., 6/4 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Mon., 6/4 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | ||
| Sat., 6/9 | V Boys Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Sat., 6/9 | V Girls Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Tue., 6/12 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/12 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/13 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||