| Fairfield Ludlowe 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 987 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | FR Baseball | New Canaan | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | TBA | Ride with varsity | With Varsity |
| TBA | JV Boys Ice Hockey | Trumbull | Home - Wonderland Of Ice [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | Joel Barlow | Away - Field J (competition field) [Directions] | TBA | ||
| TBA | JV Boys Soccer | Brien McMahon | Home - Roger Ludlowe MS [Directions] | TBA | ||
| TBA | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | TBA | PU 2:30 RE 5:30 | |
| TBA | JV Girls Lacrosse | Wilton | Home - Taft Field [Directions] | 5:30 p.m. | ||
| TBA | FR Girls Lacrosse | Trumbull | Home - Sturges Park [Directions] | TBA | ||
| TBA | FR Girls Lacrosse | Joel Barlow | Home - FLHS Front Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Westhill | Away - TBA [Directions] | TBA | Ride with Varsity | |
| TBA | JV Softball | Greenwich | Home - Tom Hayden field [Directions] | 2:00 p.m. | ||
| TBA | JV Softball | Harding | Away - Luis Marin #2 JV [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| TBA | JV Softball | Norwalk | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | New Canaan | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | TBA | PU 2:30 RE 5:30 | |
| Mon., 8/27 | V Girls Soccer | Notre Dame-Fairfield (Scrim.) | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Tue., 8/28 | V Field Hockey | Guilford (Scrim.) | Home - Taft Field [Directions] | Cancelled | ||
| Thu., 8/30 | V Boys Soccer | Fairfield Prep (Scrim.) | Home - RLMS [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | V Field Hockey | Greens Farms Academy (Scrim.) | Home - Taft Field [Directions] | 5:15 p.m. | ||
| Fri., 8/31 | V Football | Jonathan Law (Scrim.) | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Fri., 8/31 | V Girls Soccer | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 5:00 p.m. | PU:4:00 RE:7:00 | |
| Sat., 9/1 | V Field Hockey | New Fairfield Jamboree | Away - New Fairfield HS | 10:00 a.m. | PU:8:15 RE:1:30 | |
| Sat., 9/1 | V Girls Volleyball | Glastonbury Jamboree | Away | 1:00 p.m. | PU:11:30 RE:6:00 | |
| Tue., 9/4 | V Boys Soccer | Shelton (Scrim.) | Away - Capewell Park - Shelton [Directions] | 6:00 p.m. | PU:3:15 RE:6:00 | |
| Tue., 9/4 | V Field Hockey | Newtown (Scrim.) | Home - Taft Field [Directions] | 5:15 p.m. | ||
| Tue., 9/4 | V Girls Soccer | Weston (Scrim.) | Home - Sturges Park [Directions] | 3:30 p.m. | ||
| Wed., 9/5 | V Girls Volleyball | Masuk (Scrim.) | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/5 | JV Girls Volleyball | Masuk (Scrim.) | Home - FLHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/6 | FR Field Hockey | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:15 p.m. | PU:3:15 RE:5:15 | |
| Fri., 9/7 | V Football | Westhill | Home - Taft Field [Directions] | W 29-21 | ||
| Fri., 9/7 | V Boys Soccer | Danbury | Home - Roger Ludlowe MS [Directions] | T 1-1 | ||
| Fri., 9/7 | JV Boys Soccer | Danbury | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 2-0 | PU:2:15 RE:5:00 | |
| Fri., 9/7 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 3:30 p.m. | Ride with Varsity | |
| Fri., 9/7 | FR Girls Soccer | Danbury | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Sat., 9/8 | JV Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | PU:10:15 RE:1:30 | |
| Sat., 9/8 | FR Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | PU:8:15 RE:11:30 | |
| Sat., 9/8 | FR Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 2:00 p.m. | PU:12:30 RE:3:30 | |
| Sat., 9/8 | V Field Hockey | Weston | Home - Taft Field [Directions] | T 0-0 | ||
| Sat., 9/8 | JV Field Hockey | Weston | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Tue., 9/11 | V Boys Cross Country | Fairfield Warde, Norwalk, Greenwich | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | Fairfield Warde, Norwalk, Greenwich | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | L 1-3 | PU:5:15 RE:7:00 | |
| Tue., 9/11 | JV Girls Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Wed., 9/12 | V Boys Soccer | Brien McMahon | Home - Taft Field [Directions] | W 3-2 | ||
| Wed., 9/12 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | PU:4:45 RE:7:30 | |
| Wed., 9/12 | V Field Hockey | Trumbull | Home - Taft Field [Directions] | W 3-0 | ||
| Wed., 9/12 | JV Field Hockey | Trumbull | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 9/12 | FR Field Hockey | Trumbull | Away - New Turf Field [Directions] | 5:30 p.m. | PU:4:30 RE:6:30 | |
| Wed., 9/12 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | W 3-2 | PU:3:00 RE:6:30 | |
| Wed., 9/12 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 9/12 | FR Girls Volleyball | Staples | Away - Staples Field House [Directions] | 4:00 p.m. | Ride with Varsity | |
| Thu., 9/13 | FR Football | Trumbull | Home - Barlow Field [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Stamford | Home - Taft Field [Directions] | W 3-1 | ||
| Thu., 9/13 | JV Girls Soccer | Stamford | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | V Girls Swimming and Diving | Wilton | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Football | Trumbull | Away - McDougall Stadium [Directions] | L 6-47 | PU:4:30 RE:9:00 | |
| Fri., 9/14 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 2-1 | PU:2:30 RE:5:30 | |
| Fri., 9/14 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 9/14 | FR Boys Soccer | Stamford | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Competitive Cheerleading | Trumbull | Away [Directions] | 7:00 p.m. | PU:5:45 RE:9:00 | |
| Fri., 9/14 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | L 1-4 | PU:2:30 RE:6:30 | |
| Fri., 9/14 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | Ride with Varsity | |
| Fri., 9/14 | FR Field Hockey | Wilton | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Girls Volleyball | Danbury | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/14 | JV Girls Volleyball | Danbury | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Fri., 9/14 | Miscellaneous Events | Warde Vs. St. Joseph Football | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Wilton XC Invitational | Away | 9:00 a.m. | ||
| Sat., 9/15 | JV Football | Trumbull | Home - Taft Field [Directions] | 12:30 p.m. | ||
| Sat., 9/15 | V Girls Cross Country | Wilton XC Invitational | Away | 9:00 a.m. | ||
| Sat., 9/15 | V Girls Soccer | Greenwich | Home - Taft Field [Directions] | T 0-0 | ||
| Sat., 9/15 | JV Girls Soccer | Greenwich | Home - Sturges Park [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | FR Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 10:00 a.m. | PU:8:45 RE:11:30 | |
| Mon., 9/17 | V Boys Cross Country | Danbury, Darien, Trinity Catholic | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | L 1-2 | PU:3:00 RE:6:30 | |
| Mon., 9/17 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | Ride with Varsity | |
| Mon., 9/17 | FR Boys Soccer | Greenwich | Home - Roger Ludlowe MS [Directions] | 4:30 p.m. | ||
| Mon., 9/17 | V Girls Cross Country | Danbury, Darien, Trinity Catholic | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | W 4-0 | PU:2:30 RE:6:30 | |
| Mon., 9/17 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 9/17 | V Girls Soccer | New Canaan | Home - Taft Field [Directions] | W 1-0 | ||
| Mon., 9/17 | V Girls Volleyball | Brien McMahon | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Mon., 9/17 | JV Girls Volleyball | Brien McMahon | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/20 | FR Football | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Thu., 9/20 | V Girls Soccer | Ridgefield | Home - Taft Field [Directions] | L 0-2 | ||
| Thu., 9/20 | JV Girls Soccer | Ridgefield | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Girls Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/20 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/20 | V Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Thu., 9/20 | JV Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/20 | FR Girls Volleyball | Stamford | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 3-0 | PU:4:15 RE:7:30 | |
| Fri., 9/21 | JV Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 9/21 | FR Boys Soccer | Ridgefield | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | W 3-2 | PU:2:30 RE:6:30 | |
| Fri., 9/21 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | Ride with Varsity | |
| Sat., 9/22 | V Football | Norwalk | Home - Taft Field [Directions] | W 43-42 | ||
| Sat., 9/22 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 3-0 | PU:9:00 RE:12:15 | |
| Sat., 9/22 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 11:15 a.m. | Ride with Varsity | |
| Sat., 9/22 | V Girls Soccer | Trumbull | Away - New Turf Field [Directions] | L 0-1 | PU:9:45 RE:12:30 | |
| Sat., 9/22 | JV Girls Soccer | Trumbull | Away - New Turf Field [Directions] | 9:00 a.m. | PU:8:00 RE:10:30 | |
| Sat., 9/22 | FR Girls Soccer | Trumbull | Home - South Pine Creek Field [Directions] | 10:00 a.m. | ||
| Sat., 9/22 | V Girls Swimming and Diving | St. Joseph | Away - Masuk HS [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 9/24 | JV Football | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | PU:3:30 RE:6:30 | |
| Mon., 9/24 | V Boys Soccer | Trumbull | Home - Taft Field [Directions] | L 2-3 | ||
| Mon., 9/24 | JV Boys Soccer | Trumbull | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Mon., 9/24 | V Field Hockey | Staples | Home - Taft Field [Directions] | L 0-9 | ||
| Mon., 9/24 | JV Field Hockey | Staples | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 9/24 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | PU:3:00 RE:5:00 | |
| Mon., 9/24 | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 5:15 p.m. | PU:4:15 RE:6:45 | |
| Mon., 9/24 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 2-3 | PU:3:00 RE:6:30 | |
| Mon., 9/24 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 9/24 | FR Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/25 | Miscellaneous Events | Middle School Track Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | W 3-0 | PU:4:45 RE:8:15 | |
| Wed., 9/26 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | PU:2:30 RE:No | |
| Wed., 9/26 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | Ride with JV | |
| Thu., 9/27 | V Boys Cross Country | Wilton, Westhill, Staples | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/27 | FR Football | Brien McMahon | Home - Taft Field [Directions] | 7:00 p.m. | ||
| Thu., 9/27 | V Boys Soccer | Trinity Catholic | Away - Gaglio Field | W 2-0 | PU:2:30 RE:5:30 | |
| Thu., 9/27 | V Girls Cross Country | Wilton, Westhill, Staples | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 9/27 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 1-7 | PU:2:45 RE:6:30 | |
| Thu., 9/27 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Thu., 9/27 | V Girls Soccer | Trinity Catholic | Home - Taft Field [Directions] | W 7-0 | ||
| Fri., 9/28 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | W 28-27 (OT) | PU:4:30 RE:9:00 | |
| Fri., 9/28 | V Competitive Cheerleading | Brien McMahon | Away [Directions] | 7:00 p.m. | PU:5:30 RE:9:00 | |
| Fri., 9/28 | FR Field Hockey | Greenwich | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | FR Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Fri., 9/28 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | PU:2:15 RE:5:00 | |
| Fri., 9/28 | V Girls Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/28 | JV Girls Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | FR Girls Volleyball | Trumbull | Home - Ludlowe Gym [Directions] | 4:00 p.m. | PU:3:00 RE:5:00 | |
| Sat., 9/29 | JV Football | Brien McMahon | Home - Taft Field [Directions] | 1:00 p.m. | ||
| Sat., 9/29 | V Field Hockey | New Fairfield | Home - Taft Field [Directions] | L 0 - 3 | ||
| Sat., 9/29 | JV Field Hockey | New Fairfield | Home - Taft Field [Directions] | 11:30 a.m. | ||
| Mon., 10/1 | V Boys Soccer | New Canaan | Away - Dunning Stadium [Directions] | W 1-0 | PU:5:00 RE:8:00 | |
| Mon., 10/1 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/1 | FR Boys Soccer | New Canaan | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | JV Girls Soccer | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | St. Joseph, Brien McMahon, Stamford | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/2 | V Girls Cross Country | St. Joseph, Brien McMahon, Stamford | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/2 | JV Field Hockey | Darien | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 10/2 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | PU:2:45 RE:5:00 | |
| Tue., 10/2 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 5-0 | PU:3:00 RE:5:30 | |
| Wed., 10/3 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-1 | PU:2:30 RE:6:30 | |
| Wed., 10/3 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | Ride with Varsity | |
| Thu., 10/4 | FR Football | Berlin | Away - Sage Park - Scalise Field [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Bridgeport Central | Home - Taft Field [Directions] | W 4-1 | ||
| Thu., 10/4 | JV Boys Soccer | Bridgeport Central | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | FR Boys Soccer | Fairfield Prep | Away - Rafferty Stadium, Fairfield University [Directions] | 3:45 p.m. | PU:3:00 Shuttle | |
| Thu., 10/4 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 2-1(OT) | PU:2:30 RE:6:30 | |
| Thu., 10/4 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:30 p.m. | Ride with Varsity | |
| Thu., 10/4 | FR Field Hockey | Danbury | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Girls Swimming and Diving | New Canaan | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Football | Trinity Catholic | Home - Taft Field [Directions] | W 61-28 | ||
| Fri., 10/5 | V Girls Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | L 2-3 | PU:2:30 RE:5:30 | |
| Fri., 10/5 | JV Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 10/5 | FR Girls Soccer | Darien | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 2-3 | PU:2:30 RE:6:30 | |
| Fri., 10/5 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 10/5 | FR Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | V Boys Soccer | Darien | Home - Taft Field [Directions] | L 1-2 | ||
| Mon., 10/8 | JV Boys Soccer | Darien | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | FR Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/8 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University [Directions] | 4:00 p.m. | Normal shuttle to FFLD Univ. | |
| Mon., 10/8 | V Girls Volleyball | Lauralton Hall | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/8 | JV Girls Volleyball | Lauralton Hall | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Ridgefield, New Canaan, Trumbull | Away - Upper Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/9 | V Girls Cross Country | Ridgefield, New Canaan, Trumbull | Away - Upper Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/9 | V Field Hockey | Ridgefield | Home - Taft Field [Directions] | L 0-3 | ||
| Tue., 10/9 | JV Field Hockey | Ridgefield | Home - Tomlinson MS [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | St. Joseph | Home - Taft Field [Directions] | L 0-5 | ||
| Tue., 10/9 | JV Girls Soccer | St. Joseph | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | W 1-0 | PU:2:45 RE:6:00 | |
| Wed., 10/10 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | Ride with Varsity | |
| Wed., 10/10 | FR Field Hockey | Ridgefield | Away - Upper Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Wed., 10/10 | V Girls Volleyball | Bridgeport Central | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/10 | JV Girls Volleyball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Westhill | Home - Taft Field [Directions] | W 1-0 | ||
| Fri., 10/12 | JV Boys Soccer | Westhill | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | FR Girls Soccer | New Canaan | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | L 2-3 | ||
| Fri., 10/12 | JV Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Sat., 10/13 | FR Boys Soccer | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | PU:7:45 RE:10:30 | |
| Sat., 10/13 | V Field Hockey | Brien McMahon | Home - Taft Field [Directions] | OT-L 0 - 1 | ||
| Sat., 10/13 | JV Field Hockey | Brien McMahon | Home - Taft Field [Directions] | 11:30 a.m. | ||
| Sat., 10/13 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 0-3 | PU:8:45 RE:11:30 | |
| Sat., 10/13 | V Girls Volleyball | Rhode Island Volleyball Classic | Away - CCRI Lincoln, RI | TBA | TBA | No Bus |
| Mon., 10/15 | V Boys Soccer | Staples | Home - Taft Field [Directions] | L 0-2 | ||
| Mon., 10/15 | V Field Hockey | Darien | Home - Taft Field [Directions] | T 0-0 | ||
| Mon., 10/15 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | W 2-1 | PU:2:30 RE:5:30 | |
| Mon., 10/15 | V Girls Swimming and Diving | Trumbull | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 2-3 | PU:2:45 RE:6:30 | |
| Mon., 10/15 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | Ride with Varsity | |
| Mon., 10/15 | FR Girls Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | FR Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Tue., 10/16 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 0-2 | PU:5:00 RE:7:30 | |
| Tue., 10/16 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | PU:3:45 Shuttle | |
| Tue., 10/16 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | PU:3:00 shuttle | |
| Tue., 10/16 | FR Girls Soccer | Fairfield Warde | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | Miscellaneous Events | Middle School Cross Country Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | FR Football | Bridgeport Central | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 10/17 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | T 0-0 | PU:4:00 RE:6:30 | |
| Wed., 10/17 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 3-1 | PU:6:00 RE:8:30 | |
| Wed., 10/17 | V Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Wed., 10/17 | JV Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Thu., 10/18 | JV Boys Soccer | Fairfield Warde | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | PU:3:00 Shuttle | |
| Thu., 10/18 | V Field Hockey | New Canaan | Home - Taft Field [Directions] | L 1-2 | ||
| Thu., 10/18 | JV Field Hockey | New Canaan | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 10/18 | FR Field Hockey | New Canaan | Away - WTT2 [Directions] | 4:00 p.m. | PU:2:45 RE:5:00 | |
| Thu., 10/18 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Thu., 10/18 | V Girls Swimming and Diving | Darien | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Football | Montville | Away - Montville H.S. [Directions] | W 47-12 | PU:2:00 RE:8:30 | |
| Fri., 10/19 | JV Boys Soccer | Staples | Home - Roger Ludlowe MS [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Competitive Cheerleading | Montville | Away [Directions] | 6:30 p.m. | PU:4:00 RE:8:30 | |
| Fri., 10/19 | V Girls Soccer | Norwalk | Home - Taft Field [Directions] | W 3-0 | ||
| Fri., 10/19 | JV Girls Soccer | Norwalk | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Fri., 10/19 | JV Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | Staples | Home - FLHS Aux Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/20 | JV Football | Nonnewaug | Home - Taft Field [Directions] | 12:00 p.m. | ||
| Sat., 10/20 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 2-1 | PU:8:30 RE:11:30 | |
| Sat., 10/20 | JV Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 10:00 a.m. | Ride with Varsity | |
| Sat., 10/20 | FR Boys Soccer | Norwalk | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Mon., 10/22 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 3-0 | PU:4:30 RE:7:30 | |
| Mon., 10/22 | V Field Hockey | Westhill | Away - Westhill Stadium [Directions] | W 4-0 | PU:2:30 RE:6:30 | |
| Mon., 10/22 | JV Field Hockey | Westhill | Away - Westhill Football Field [Directions] | 5:30 p.m. | Ride with Varsity | |
| Mon., 10/22 | FR Field Hockey | Westhill | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Soccer | Wilton | Home - Taft Field [Directions] | L 0-1 | ||
| Mon., 10/22 | JV Girls Soccer | Wilton | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/22 | V Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/22 | JV Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 10/22 | FR Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 10/23 | JV Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 10/23 | FR Boys Soccer | Wilton | Home - Roger Ludlowe MS [Directions] | 4:30 p.m. | ||
| Tue., 10/23 | FR Girls Soccer | Staples | Home - South Pine Creek Field [Directions] | 3:30 p.m. | ||
| Tue., 10/23 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 10/24 | V Field Hockey | Norwalk | Home - Taft Field [Directions] | L 1 - 5 | ||
| Wed., 10/24 | JV Field Hockey | Norwalk | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 10/24 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | W 3-0 | PU:2:30 RE:6:30 | |
| Wed., 10/24 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | Ride with Varsity | |
| Thu., 10/25 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | L 7-56 | PU:2:15 RE:7:00 | |
| Thu., 10/25 | FR Football | Greenwich | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 10/25 | V Competitive Cheerleading | Greenwich | Away [Directions] | 6:00 p.m. | PU:4:30 RE:8:00 | |
| Fri., 10/26 | JV Football | Greenwich | Away - Field 7 [Directions] | 4:00 p.m. | ||
| Fri., 10/26 | V Boys Soccer | Fairfield Warde | Home - Taft Field [Directions] | W 2-0 | ||
| Fri., 10/26 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 3-0 | PU:2:30 RE:6:30 | |
| Fri., 10/26 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | Ride with Varsity | |
| Fri., 10/26 | FR Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 10/29 | V Boys Soccer | Danbury | Home - Taft Field [Directions] | L 0-1 | ||
| Tue., 10/30 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-0 | ||
| Thu., 11/1 | V Football | Danbury | Home - Taft Field [Directions] | W 45-39 | ||
| Fri., 11/2 | FR Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | PU:2:15 RE:5:30 | |
| Mon., 11/5 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:00 p.m. | PU:3:15 RE:6:30 | |
| Mon., 11/5 | V Field Hockey | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 11/5 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Mon., 11/5 | V Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 11/6 | V Boys Soccer | East Hartford | Home - Taft Field [Directions] | L 0-2 | ||
| Wed., 11/7 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/8 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | PU:3:30 RE:6:30 | |
| Thu., 11/8 | V Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/9 | V Football | New Canaan | Home - Taft Field [Directions] | L 7-41 | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | ||
| Mon., 11/12 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/17 | JV Football | Fairfield Warde | Home - Taft Field [Directions] | 12:00 p.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Tue., 11/20 | FR Football | Fairfield Warde | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 11/21 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 34-33 | PU:8:30 RE:12:00 | |
| Thu., 11/22 | V Competitive Cheerleading | Fairfield Warde | Away [Directions] | 10:00 a.m. | PU:9:00 RE:12:00 | |
| Sat., 12/1 | V Boys Ice Hockey | Greenwich (Scrim.) | Away - Dorothy Hamill Ice Rink [Directions] | 6:30 p.m. | PU at Wonderland 4:45 RE 8:00 | |
| Sat., 12/1 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 10:00 a.m. | No Bus | |
| Sat., 12/1 | V Girls Ice Hockey | FCIAC Jamboree | Away - The Rinks at Shelton | TBA | No Bus | |
| Mon., 12/3 | V Girls Basketball | Masuk (Scrim.) | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Tue., 12/4 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 4:30 p.m. | PU 3:15 RE 6:00 | |
| Tue., 12/4 | V Girls Basketball | Seymour (Scrim.) | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | Masuk Coop (Scrim.) | Home - Wonderland of Ice [Directions] | 3:15 p.m. | ||
| Thu., 12/6 | V Boys Basketball | Joel Barlow (Scrim.) | Away - JBHS Lower Gym [Directions] | 5:30 p.m. | PU 4:00 RE 7:00 | |
| Sat., 12/8 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - FLHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 12/8 | V Girls Basketball | Greenwich (Scrim.) | Away - GHS Gymnasium [Directions] | 12:00 p.m. | PU 10:45 RE 12:30 | |
| Wed., 12/12 | V Wrestling | Staples | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | V Girls Basketball | Norwalk | Home - FLHS Main Gym [Directions] | L 35-58 | ||
| Wed., 12/12 | JV Girls Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | T 2-2(OT) | PU 6:15 RE 10:00 | |
| Thu., 12/13 | V Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | L 61-63 | PU 3:45 RE 8:30 | |
| Thu., 12/13 | JV Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:15 p.m. | Ride with varsity | |
| Thu., 12/13 | FR Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 3:45 p.m. | PU 2:30 RE 5:00 | |
| Fri., 12/14 | JV Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | PU at Wonderland 7:00 RE 10:00 | |
| Fri., 12/14 | V Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | W 44-40 | ||
| Fri., 12/14 | JV Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | West Haven Coop | Home - Wonderland Of Ice [Directions] | L 3-5 | ||
| Sat., 12/15 | V Boys Indoor Track | Staples, St. Joseph, Ridgefield, Trumbull | Away | 10:00 a.m. | PU 8:45 RE 2:00 | |
| Sat., 12/15 | V Wrestling | Ludlowe Invitational | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Wonderland of Ice [Directions] | W 9-3 | ||
| Sat., 12/15 | V Girls Indoor Track | Staples | Away [Directions] | 10:00 a.m. | PU 8:45 RE 2:00 | |
| Wed., 12/19 | V Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | W 41-39 | ||
| Wed., 12/19 | JV Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - Wonderland Of Ice [Directions] | W 7-3 | ||
| Wed., 12/19 | V Wrestling | Greenwich | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 53-60 | PU 3:00 RE 8:30 | |
| Wed., 12/19 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | Ride with varsity | |
| Wed., 12/19 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | PU 2:45 RE 5:15 | |
| Wed., 12/19 | V Girls Ice Hockey | Greenwich | Home - Wonderland of Ice [Directions] | L 0-3 | ||
| Fri., 12/21 | V Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | L 48-62 | ||
| Fri., 12/21 | JV Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | JV Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 5:30 p.m. | PU at Wonderland 6:30 RE 9:30 | |
| Fri., 12/21 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 58-47 | PU 2:45 RE 7:00 | |
| Fri., 12/21 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | Ride with varsity | |
| Fri., 12/21 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks [Directions] | W 5-1 | PU 5:30 RE 9:45 | |
| Sat., 12/22 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena - Rt 5 [Directions] | L 3-4 | PU at Wonderland 12:30 RE 4:30 | |
| Sat., 12/22 | V Wrestling | Simsbury Invitational | Away | 9:00 a.m. | PU 6:15 RE 6:00 | |
| Thu., 12/27 | V Boys Basketball | Fairfield Prep | Away - Alumni Hall, Fairfield University [Directions] | W 46-42 | No Bus | |
| Thu., 12/27 | JV Boys Basketball | Fairfield Prep | Home - FLHS Main Gym [Directions] | 10:00 a.m. | ||
| Thu., 12/27 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | W 2-1 | PU at Wonderland 4:30 RE 8:30 | |
| Thu., 12/27 | V Girls Basketball | St. Paul Catholic | Away - Fairfield Warde [Directions] | W 38-35(OT) | No bus | |
| Thu., 12/27 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 10:00 a.m. | No bus | |
| Fri., 12/28 | V Boys Basketball | Fairfield Warde | Away - Fairfield University [Directions] | L 37-38 | No Bus | |
| Fri., 12/28 | JV Boys Basketball | Holiday Tournament | Home - FLHS Main Gym [Directions] | TBA | ||
| Fri., 12/28 | V Girls Basketball | Staples | Away - Fairfield Warde [Directions] | W 48-36 | No bus | |
| Sat., 12/29 | V Boys Ice Hockey | St. Joseph | Home - Wonderland Of Ice [Directions] | W 4-0 | ||
| Sat., 12/29 | V Boys Indoor Track | Marine Corps Holiday Classic | Away | 8:00 a.m. | No Bus | at Armory |
| Sat., 12/29 | V Wrestling | Trumbull Duals | Away | 9:30 a.m. | PU 7:30 RE 6:00 | |
| Sat., 12/29 | V Girls Indoor Track | Marine Corps Holiday Classic | Away | 8:00 a.m. | No Bus | At Armory |
| Thu., 1/3 | V Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | L 49-52 | PU 3:30 RE 8:30 | |
| Thu., 1/3 | JV Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | Ride with varsity | |
| Thu., 1/3 | FR Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Thu., 1/3 | V Wrestling | Brien McMahon | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/3 | V Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | W 50-39 | ||
| Thu., 1/3 | JV Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | FR Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/3 | V Girls Gymnastics | Darien, Oxford | Home - GCA [Directions] | Ludlowe- 130.00 Oxford- 129.15 Warde- 126.40 Darien- 119.00 | ||
| Thu., 1/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Wonderland of Ice [Directions] | W 13-6 | ||
| Fri., 1/4 | JV Boys Ice Hockey | Ridgefield | Home - Wonderland Of Ice [Directions] | 4:50 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | PU W 2:00 L 2:15; RE 5:30 | |
| Sat., 1/5 | V Boys Indoor Track | Elm City Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | PU:7:30 RE:2:30 | |
| Sat., 1/5 | V Boys Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Sat., 1/5 | V Wrestling | Fairfield Warde Invitational | Away | 9:30 a.m. | PU 7:00 No Return | |
| Sat., 1/5 | V Girls Gymnastics | Pomperaug Invitational | Away - Pomperaug HS | 133.70 1st place | PU 8:15 at Ludlowe, 8:30 at Warde RE 1:00 | |
| Sat., 1/5 | V Girls Indoor Track | Elm City Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | Ride with Boys | |
| Sat., 1/5 | V Girls Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Mon., 1/7 | V Boys Basketball | Greenwich | Away - Brunswick School [Directions] | W 47-43 | PU 3:15 RE 8:30 | |
| Mon., 1/7 | V Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | W 55-22 | ||
| Mon., 1/7 | JV Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/8 | V Girls Gymnastics | Foran | Home - GCA in Fairfield [Directions] | 130.15 | PU 4:45 at Ludlowe RE 8:30 | |
| Tue., 1/8 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-7 | PU 3:30 RE 7:30 | |
| Wed., 1/9 | V Boys Ice Hockey | Greenwich | Home - Wonderland Of Ice [Directions] | T 5-5(OT) | ||
| Wed., 1/9 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | PU L 2:30, W 2:45 RE 5:30 | |
| Wed., 1/9 | V Wrestling | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:00 p.m. | PU 3:15 RE 6:15 | |
| Thu., 1/10 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 53-61 | PU 3:15 RE 8:30 | |
| Thu., 1/10 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | Ride with Varsity | |
| Thu., 1/10 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Thu., 1/10 | V Co-ed Alpine Skiing | Staples | Home - Mt. Southington [Directions] | TBA | PU Ludlowe 1:40 PU Warde 1:50 RE 6:30 | Also Cheshire, Amity, Brookfield, Bethal, Glastonbury, Farmington and New Canaan |
| Thu., 1/10 | V Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | W 57-53(OT) | ||
| Thu., 1/10 | JV Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/11 | JV Boys Ice Hockey | Greenwich | Home - Wonderland Of Ice [Directions] | 4:50 p.m. | ||
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational | Away | TBA | PU 11:20 RE 4:15 | |
| Fri., 1/11 | V Girls Gymnastics | Daniel Hand, Fairfield Warde | Home - GCA [Directions] | Ludlowe- 131.70 Warde- 125.30 Daniel Hand- 118.70 | ||
| Fri., 1/11 | V Girls Indoor Track | Yale Invitational | Away | TBA | PU 11:20 RE 4:15 | |
| Sat., 1/12 | JV Boys Basketball | Greenwich | Away - Central MS [Directions] | 10:30 a.m. | PU 7:45 RE 11:30 | |
| Sat., 1/12 | FR Boys Basketball | Greenwich | Away - Central MS [Directions] | 9:00 a.m. | Ride with JV | |
| Sat., 1/12 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | W 4-2 | PU at Wonderland 6:30 RE 9:30 | |
| Sat., 1/12 | V Boys Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Sat., 1/12 | V Boys Indoor Track | Yale Invitational | Away | TBA | No Bus | |
| Sat., 1/12 | V Wrestling | Daniel Hand Duals | Away | 9:00 a.m. | PU 6:30 RE 4:00 | |
| Sat., 1/12 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - The Rinks at Shelton [Directions] | W 10-2 | PU 6:15 RE 9:00 | |
| Sat., 1/12 | V Girls Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Sat., 1/12 | V Girls Indoor Track | Yale Invitational | Away | TBA | No Bus | |
| Mon., 1/14 | V Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | L 64-77 | ||
| Mon., 1/14 | JV Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | V Boys Ice Hockey | Staples | Home - Wonderland Of Ice [Directions] | W 7-2 | ||
| Mon., 1/14 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 33-51 | PU 4:00 RE 8:30 | |
| Mon., 1/14 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | Ride with varsity | |
| Mon., 1/14 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | PU 2:45 RE 5:15 | |
| Mon., 1/14 | V Girls Gymnastics | Westhill, New Canaan | Home - GCA [Directions] | Ludlowe- 136.05 New Canaan- 118.50 Westhill- 112.00 | ||
| Mon., 1/14 | V Girls Ice Hockey | Darien | Home - Wonderland of Ice [Directions] | L 1-5 | ||
| Wed., 1/16 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | W 5-2 | PU at Wonderland 6:30 RE 10:00 | |
| Wed., 1/16 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | PU W 1:30, L 1:45 RE 4:30 | |
| Wed., 1/16 | V Wrestling | Darien | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/17 | V Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | W 62-60 | ||
| Thu., 1/17 | JV Boys Basketball | Harding | Home - FLHS Aux Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/17 | FR Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | V Girls Basketball | Bassick | Home - FLHS Main Gym [Directions] | W 65-46 | ||
| Thu., 1/17 | JV Girls Basketball | Bassick | Home - FLHS Main Gym [Directions] | Cancelled | ||
| Thu., 1/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Wonderland of Ice [Directions] | W 3-1 | ||
| Fri., 1/18 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | L 2-8 | PU at Wonderland 6:30 RE 10:00 | |
| Fri., 1/18 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 5:30 p.m. | PU at Wonderland 4:00 RE 7:00 | |
| Fri., 1/18 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:00 p.m. | PU W 2:15, L 2:30 RE 5:30 | |
| Fri., 1/18 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | Ludlowe- 137.20 Greenwich- 135.00 | PU 4:00 at Warde, 4:15 at Ludlowe RE 8:00 | |
| Sat., 1/19 | V Boys Indoor Track | – SCC Coaches’ Invitational | Away - Hillhouse | 9:00 a.m. | PU 7:45 RE 2:00 | |
| Sat., 1/19 | V Boys Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Sat., 1/19 | V Wrestling | New Milford Invitational | Away | 9:00 a.m. | PU 6:00 RE 6:00 | |
| Sat., 1/19 | V Competitive Cheerleading | Ludlowe Cheer Competition | Home - FLHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 1/19 | V Co-ed Fencing | Hopkins School | Away | 10:00 a.m. | PU at Warde 8:00, RE 2:30 | |
| Sat., 1/19 | V Girls Ice Hockey | Hall/Conard | Home - Wonderland of Ice [Directions] | L 1-4 | ||
| Sat., 1/19 | V Girls Indoor Track | SCC Coaches’ Invitational | Away - Hillhouse | 9:00 a.m. | PU 7:45 RE 2:00 | |
| Sat., 1/19 | V Girls Indoor Track | Wilton | Away [Directions] | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Mon., 1/21 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-3 | PU at Wonderland 3:30 RE 6:30 | |
| Tue., 1/22 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | W 45-43 | PU 3:30 RE 8:30 | |
| Tue., 1/22 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | Ride with varsity | |
| Tue., 1/22 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Tue., 1/22 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena [Directions] | 8:00 p.m. | PU at Wonderland at 6:00 RE 9:30 | |
| Tue., 1/22 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | PU W 2:00, L 2:15 RE 5:15 | |
| Tue., 1/22 | V Girls Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | L 44-51 | ||
| Tue., 1/22 | JV Girls Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Wrestling | Trumbull | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/23 | V Co-ed Alpine Skiing | Greenwich | Home - Mt. Southington [Directions] | TBA | PU Ludlowe 1:40 PU Warde 1:50 RE 6:30 | Also Litchfield, Barlow, Westbrook, St. Lukes |
| Wed., 1/23 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy [Directions] | W 54-23 | PU 2:15 RE 7:30 | |
| Wed., 1/23 | JV Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 1/23 | V Girls Gymnastics | Trumbull, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | Ludlowe- 132.85 Trumbull- 128.65 | ||
| Wed., 1/23 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | W 8-1 | PU 6:00 RE 9:45 | |
| Thu., 1/24 | JV Wrestling | Fairfield Warde, Fairfield Prep | Away [Directions] | 3:30 p.m. | PU 2:40 RE 5:00 | |
| Thu., 1/24 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 3-6 | PU 6:00 RE 9:45 | |
| Fri., 1/25 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | L 26-39 | PU 3:15 RE 8:30 | |
| Fri., 1/25 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | Ride with varsity | |
| Fri., 1/25 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Fri., 1/25 | JV Boys Ice Hockey | Darien | Home - Wonderland Of Ice [Directions] | 4:50 p.m. | ||
| Fri., 1/25 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | PU L 2:00, W 2:15; RE 6:00 | |
| Fri., 1/25 | V Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | W 36-32 | ||
| Fri., 1/25 | JV Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/26 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | L 1-4 | PU at Wonderland 1:00 RE 5:00 | |
| Sat., 1/26 | V Boys Indoor Track | Eastern Division Championship | Away - Wilton | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Sat., 1/26 | V Wrestling | Southington Invitational | Away | 9:00 a.m. | PU 6:30 RE 6:00 | |
| Sat., 1/26 | V Competitive Cheerleading | Battle at St. Joe's | Away | TBA | No Bus | |
| Sat., 1/26 | V Co-ed Fencing | Guilford | Away [Directions] | 9:00 a.m. | PU at Warde 7:30, RE 5:00 | |
| Sat., 1/26 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | L 1-4 | PU 1:15 RE 4:30 | |
| Sat., 1/26 | V Girls Indoor Track | Eastern Division Championship | Away | 9:30 a.m. | PU 8:00 RE 2:00 | |
| Tue., 1/29 | V Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | W 61-52 | ||
| Tue., 1/29 | JV Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/29 | FR Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - SoNo Ice House [Directions] | W 10-0 | PU at Wonderland 7:00 RE 10:00 | |
| Tue., 1/29 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 72-20 | PU 3:00 RE 7:00 | |
| Tue., 1/29 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | Ride with varsity | |
| Thu., 1/31 | V Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | L 71-74(2OT) | ||
| Thu., 1/31 | JV Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | JV Boys Ice Hockey | St. Joseph | Home - Wonderland Of Ice [Directions] | 4:45 p.m. | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championship | Away - Floyd Little AC | 4:30 p.m. | PU 2:30 RE 9:30 | |
| Thu., 1/31 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:15 p.m. | PU W 1:30, L 1:45; RE 4:45 | |
| Thu., 1/31 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | W 51-35 | PU 4:00 RE 8:30 | |
| Thu., 1/31 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | Ride with varsity | |
| Thu., 1/31 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | PU 3:20 RE 5:15 | |
| Thu., 1/31 | V Girls Gymnastics | Staples | Home - GCA [Directions] | Ludlowe- 136.20 Staples- 124.05 | ||
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championship | Away | 4:30 p.m. | PU 3:20 RE 9:30 | |
| Fri., 2/1 | V Wrestling | Danbury, New Canaan | Away - Danbury HS New Gym [Directions] | 4:30 p.m. | PU 2:30 RE 6:30 | |
| Sat., 2/2 | V Boys Indoor Track | FCIAC JV/Last Chance Meet | Away - Staples HS | 10:00 a.m. | No Bus | |
| Sat., 2/2 | JV Wrestling | Ludlowe JV Invitational | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/2 | V Competitive Cheerleading | FCIAC's | Away | TBA | PU 8:45 RE 2:30 | |
| Sat., 2/2 | V Co-ed Fencing | Greens Farms Academy | Home - Fairfield Warde Small Gym [Directions] | 2:00 p.m. | Prospect is competing as well | |
| Sat., 2/2 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 10-1 | PU 6:45 RE 9:45 | |
| Sat., 2/2 | V Girls Indoor Track | FCIAC JV/Last Chance Meet | Away - Staples HS | 10:00 a.m. | No Bus | |
| Mon., 2/4 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | 8:40 p.m. | PU at Wonderland 7:00 RE 10:00 | |
| Mon., 2/4 | V Wrestling | Norwalk | Away - Scarso Gymnasium [Directions] | 7:00 p.m. | PU 2:30 RE 5:30 | |
| Tue., 2/5 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | L 55-63 | PU 3:30 RE 8:30 | |
| Tue., 2/5 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | Ride with varsity | |
| Tue., 2/5 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Tue., 2/5 | V Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | W 41-37 | ||
| Tue., 2/5 | JV Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | V Girls Gymnastics | Wilton, Fairfield Warde | Away [Directions] | Wilton- 139.50 Ludlowe- 138.35 | PU 3:00 Warde, 3:15 Ludlowe RE 7:00 | |
| Wed., 2/6 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 2-9 | PU at Wonderland 4:00 RE 7:30 | |
| Wed., 2/6 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Unknown [Directions] | 3:30 p.m. | PU at Warde at 2:00 PU at Ludlowe at 2:15; RE 4:45 | |
| Wed., 2/6 | V Wrestling | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | PU 4:15 RE 7:30 | |
| Wed., 2/6 | V Girls Ice Hockey | New Canaan | Home - Wonderland of Ice [Directions] | L 0-4 | ||
| Thu., 2/7 | V Co-ed Alpine Skiing | Darien | Home - Mt. Southington [Directions] | TBA | PU Ludlowe 1:40 PU Warde 1:50 RE 6:30 | Also, Guilford, Danbury, Lauralton, New Fairfield, Southington, Hand, Wamogo, Weston |
| Thu., 2/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Wonderland of Ice [Directions] | W 7-4 | ||
| Fri., 2/8 | V Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | W 60-32 | ||
| Fri., 2/8 | JV Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | PU at Wonderland 7:30 RE 10:30 | |
| Fri., 2/8 | V Boys Swimming and Diving | New Canaan | Home - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Wrestling | FCIAC Wrestling Championships | Away - New Canaan HS | 4:30 p.m. | PU 2:15 No Return | |
| Fri., 2/8 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 53-45 | PU 2:45 RE 7:00 | |
| Fri., 2/8 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Ride with varsity | |
| Sat., 2/9 | V Boys Ice Hockey | Darien | Home - Wonderland Of Ice [Directions] | L 0-6 | ||
| Sat., 2/9 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | PU 2:30 RE 9:00 | |
| Sat., 2/9 | V Wrestling | FCIAC Wrestling Championships | Away - New Canaan HS | 10:00 a.m. | PU 8:30 No Return | |
| Sat., 2/9 | V Competitive Cheerleading | Warde Cheer Challenge | Away | TBA | No Bus | |
| Sat., 2/9 | V Co-ed Fencing | Hopkins School | Away | 10:00 a.m. | PU at Warde 8:00, RE 2:30 | |
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championships | Away - Westhill HS | Ludlowe- 133.90 2nd | PU at Ludlowe 8:30 RE 1:30 | |
| Sat., 2/9 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | PU 2:30 RE 9:00 | |
| Mon., 2/11 | V Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | W 57-26 | ||
| Mon., 2/11 | JV Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 42-48 | PU 4:00 RE 8:30 | |
| Mon., 2/11 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | Ride with varsity | |
| Mon., 2/11 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | PU 2:45 RE 5:15 | |
| Mon., 2/11 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Wonderland of Ice [Directions] | W 3-0 | ||
| Wed., 2/13 | V Boys Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | L 32-44 | ||
| Wed., 2/13 | JV Boys Basketball | Fairfield Warde | Home - FLHS Aux Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/13 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners Ice Rink [Directions] | L 4-5(OT) | PU at Wonderland 6:00 RE 9:30 | |
| Wed., 2/13 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | PU W 2:30, L 2:45; RE 5:30 | |
| Wed., 2/13 | V Co-ed Alpine Skiing | Ridgefield | Home - Mt. Southington [Directions] | TBA | PU Ludlowe 1:40 PU Warde 1:50 RE 6:30 | Also, Brunswick and Prep |
| Wed., 2/13 | V Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | L 34-54 | ||
| Wed., 2/13 | JV Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/13 | V Girls Gymnastics | Fairfield Warde | Home - GCA [Directions] | Ludlowe- 136.45 Warde- 124.70 | ||
| Wed., 2/13 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-7 | PU 5:45 RE 8:45 | |
| Thu., 2/14 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:45 p.m. | PU 5:45 No Return | |
| Thu., 2/14 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:00 p.m. | PU 4:00 No Return | |
| Fri., 2/15 | JV Boys Ice Hockey | New Canaan | Home - Wonderland Of Ice [Directions] | 4:40 p.m. | ||
| Fri., 2/15 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:45 p.m. | PU 1:00 No Return | |
| Fri., 2/15 | V Girls Ice Hockey | Avon | Home - Wonderland of Ice [Directions] | W 4-3 | ||
| Sat., 2/16 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | W 7-1 | PU at Wonderland 4:30 RE 7:30 | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | No Bus | |
| Sat., 2/16 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | No bus | |
| Sat., 2/16 | V Co-ed Fencing | North Haven | Home - Fairfield Warde Small Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | No Bus | |
| Mon., 2/18 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | W 47-37 | PU 3:30 RE 8:30 | |
| Mon., 2/18 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | Ride with varsity | |
| Mon., 2/18 | FR Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Mon., 2/18 | V Boys Ice Hockey | Trumbull | Home - Wonderland Of Ice [Directions] | W 5-4 | ||
| Wed., 2/20 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 6:00 p.m. | PU 4:30 RE 8:15 | FCIAC Semi-Finals |
| Thu., 2/21 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | L 58-75 | PU 3:30 RE 8:30 | |
| Thu., 2/21 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | Ride with JV | |
| Thu., 2/21 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Thu., 2/21 | V Boys Ice Hockey | Wilton | Home - Wonderland Of Ice [Directions] | W 7-2 | ||
| Fri., 2/22 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | W 5-4 | PU at Wonderland 5:30 RE 9:30 | |
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | No Bus | |
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | No Bus | |
| Sat., 2/23 | V Competitive Cheerleading | Mercy Tigers Cheer Challenge | Away | 10:00 a.m. | PU 8:00 RE 1:30 | |
| Sat., 2/23 | V Co-ed Fencing | JV Tournament | Away - North Haven HS | 10:00 a.m. | PU 7:30 RE 3:30 | |
| Sat., 2/23 | Winter Dance Team | State Championship | Away | 11:00 a.m. | PU 8:00 RE 3:30 | |
| Sat., 2/23 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law HS [Directions] | TBA | ||
| Mon., 2/25 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks [Directions] | 8:10 p.m. | PU 5:30 RE 9:30 | State Tournament First Round |
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Swimming Trials | Away - Greenwich HS | 5:30 p.m. | PU 2:00 at Warde, 2:15 at Ludlowe RE 8:45 | |
| Tue., 2/26 | V Co-ed Alpine Skiing | Wilton | Home - Mt. Southington [Directions] | TBA | PU Ludlowe 1:40 PU Warde 1:50 RE 6:30 | Also, Cheshire Academy, Pomperaug, Gilbert, Westhill, Hopkins |
| Tue., 2/26 | V Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/27 | V Co-ed Fencing | North Haven | Away [Directions] | Cancelled | ||
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Swimming Championship | Away | 6:30 p.m. | PU 3:30 (Warde only) RE 8:45 | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | TBA | |
| Sun., 3/3 | V Competitive Cheerleading | CIAC Cheerleading Championships | Away - Floyd Little Athletic Center | TBA | PU 3:00 RE 6:30 | |
| Tue., 3/5 | V Boys Basketball | Cheshire | Away - Cheshire High - West Gym [Directions] | 7:00 p.m. | PU 4:15 RE 8:30 | |
| Tue., 3/5 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 6:00 p.m. | PU at Wonderland 4:45 RE 7:30 | Division I First Round |
| Tue., 3/5 | V Co-ed Alpine Skiing | Ski State Tournament | Away - Mt. Southington | TBA | PU 12:15 Ludlowe; 12:30 Warde RE 6:00 | |
| Wed., 3/6 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | PU 5:30 RE 8:30 | CIAC Division II Second Round |
| Wed., 3/6 | V Girls Gymnastics | CIAC Open Championship | Away - New Milford HS [Directions] | 4:00 p.m. | PU 1:30 at Ludlowe, 1:45 at Warde RE 7:00 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | No Bus | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford HS [Directions] | 6:00 p.m. | PU 2:30 (Warde Only) RE 7:30 | |
| Sat., 3/9 | V Co-ed Fencing | State Individual Tournament | Away - Guilford HS | TBA | PU 7:00 RE 2:00 | |
| Sun., 3/10 | V Co-ed Fencing | State Individual Tournament | Away - Guilford HS | TBA | PU 7:00 RE 2:00 | |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 1:30 p.m. | PU 10:30 at Ludlowe, 10:45 at Warde RE 4:00 | |
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | No bus | |
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | PU 3:45 RE 9:00 | |
| Sat., 3/16 | V Co-ed Fencing | Team State Tournament | Away - Fitch HS | TBA | PU 7:00 RE 3:00 | |
| Wed., 3/20 | V Co-ed Sailing | Fairfield Prep | Home - Pequot YC [Directions] | 3:30 p.m. | ||
| Thu., 3/21 | V Girls Lacrosse | Daniel Hand (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 3/21 | V Softball | Jonathan Law (Scrim.) | Away - Jonathan Law HS Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 12:00 p.m. | PU 11:30 RE 2:00 | |
| Sat., 3/23 | V Boys Volleyball | Glastonbury (Scrim.) | Away [Directions] | 9:00 a.m. | PU:7:30 RE:2:30 | |
| Sat., 3/23 | V Girls Lacrosse | Staples (Scrim.) | Away [Directions] | 9:00 a.m. | PU 8:00 RE 1:15 | |
| Sun., 3/24 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS [Directions] | 12:00 p.m. | PU 10:30 RE 2:30 | |
| Mon., 3/25 | V Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 3:45 p.m. | No Bus | |
| Mon., 3/25 | JV Baseball | Fairfield Warde (Scrim.) | Home - Kiwanis Field [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | FR Baseball | Fairfield Warde (Scrim.) | Away - Owen Fish Park [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Joel Barlow (Scrim.) | Away - Field E (Softball) [Directions] | 3:45 p.m. | PU 2:15 RE 5:15 | |
| Tue., 3/26 | V Baseball | Bunnell (Scrim.) | Home - Kiwanis Field [Directions] | 4:30 p.m. | ||
| Tue., 3/26 | V Boys Volleyball | Kolbe Cathedral (Scrim.) | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | Fairfield Prep (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Guilford (Scrim.) | Away - Kavanaugh Turf Field at GHS [Directions] | 6:00 p.m. | PU 4:45 RE 7:45 | |
| Wed., 3/27 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:30 p.m. | PU 2:25 RE 5:30 | |
| Thu., 3/28 | V Baseball | Branford (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | Joel Barlow (Scrim.) | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Softball | Cheshire (Scrim.) | Home - Dougiello Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | JV Softball | Cheshire (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 3/29 | V Boys Tennis | Joel Barlow (Scrim.) | Away - Tennis Courts [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Sat., 3/30 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Taft Field [Directions] | 8:00 a.m. | ||
| Sat., 3/30 | FR Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Tomlinson MS, Fairfield, CT [Directions] | 8:30 a.m. | No Bus | |
| Mon., 4/1 | V Baseball | Joel Barlow | Home - Kiwanis Field [Directions] | W 6-5 (8) | ||
| Mon., 4/1 | JV Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Mon., 4/1 | FR Baseball | Fairfield Prep | Away - Owen Fish Park [Directions] | 3:45 p.m. | Shuttle | |
| Mon., 4/1 | V Boys Outdoor Track | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | PU 2:05 RE 6:45 | |
| Mon., 4/1 | V Boys Tennis | Danbury | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/1 | V Girls Outdoor Track | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | PU 2:05 RE 6:45 | |
| Mon., 4/1 | V Softball | Middletown | Away - Middletown HS [Directions] | W 11-1 | PU 2:05 RE 5:30 | |
| Mon., 4/1 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | W 7-0 | PU 2:30 RE 5:30 | |
| Tue., 4/2 | V Boys Lacrosse | Xavier | Home - Taft Field [Directions] | W 7-4 | ||
| Tue., 4/2 | JV Boys Lacrosse | Xavier | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 4/2 | V Boys Tennis | Brien McMahon | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/2 | JV Boys Tennis | Weston | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | W 15-5 | PU 2:30 RE 6:30 | |
| Tue., 4/2 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | Ride with varsity | |
| Tue., 4/2 | JV Girls Tennis | Weston | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Baseball | Naugatuck | Home - Kiwanis Field [Directions] | W 16-5 (6) | ||
| Wed., 4/3 | JV Baseball | Fairfield Prep | Away - Owen Fish Park [Directions] | 3:45 p.m. | Shuttle | |
| Wed., 4/3 | FR Baseball | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Wed., 4/3 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Wed., 4/3 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 1-3 | PU 3:00 RE 7:00 | |
| Wed., 4/3 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | Ride with varsity | |
| Wed., 4/3 | V Co-ed Sailing | Greenwich Academy | Away - Grass Island | 3:30 p.m. | PU 2:25 RE 5:30 | |
| Wed., 4/3 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | Ludlowe: 191 Darien: 204 | PU 2:10 RE 4:30 | |
| Wed., 4/3 | FR Girls Lacrosse | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | L 0-12 | PU 2:20 RE 5:30 | |
| Wed., 4/3 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | PU 2:30 RE 5:30 | |
| Wed., 4/3 | JV Girls Tennis | Fairfield Warde | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | FR Baseball | North Haven | Away - Bailey Road Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Thu., 4/4 | V Boys Golf | Fairfield Warde, Danbury | Home - Brooklawn Country Club [Directions] | Ludlowe 186/ Danbury 196 | No Bus | |
| Thu., 4/4 | V Boys Tennis | Stamford | Away [Directions] | W 7-0 | PU 2:30 RE 5:30 | |
| Thu., 4/4 | JV Boys Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Thu., 4/4 | V Girls Lacrosse | Middletown/Coginchaug | Home - Taft Field [Directions] | W 15-1 | ||
| Thu., 4/4 | V Girls Tennis | Stamford | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Thu., 4/4 | JV Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Fri., 4/5 | V Boys Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | L 2-3 | ||
| Fri., 4/5 | JV Boys Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 4/6 | V Baseball | North Haven | Home - Kiwanis Field [Directions] | W 6-5 (8) | ||
| Sat., 4/6 | JV Baseball | North Haven | Home - Tunxis Hill Park [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Boys Lacrosse | Cheshire | Away - West Point, NY [Directions] | W 11-5 | No Bus | |
| Sat., 4/6 | V Girls Lacrosse | Brien McMahon | Home - Taft Field [Directions] | W 17-3 | ||
| Sat., 4/6 | JV Girls Lacrosse | Brien McMahon | Home - Taft Field [Directions] | 11:30 a.m. | ||
| Mon., 4/8 | V Baseball | Danbury | Home - Kiwanis Field [Directions] | W 4-3 (11) | ||
| Mon., 4/8 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 | PU 3:00 RE 6:00 | |
| Mon., 4/8 | V Boys Volleyball | Darien | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Mon., 4/8 | JV Boys Volleyball | Darien | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | V Girls Outdoor Track | Darien, St. Joseph | Away - DHS Stadium Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Mon., 4/8 | V Girls Tennis | Greenwich | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | ||
| Mon., 4/8 | JV Girls Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Tue., 4/9 | V Boys Golf | St. Joseph | Away [Directions] | Ludlowe 176/ St. Joseph 198 | PU 2:15 RE 5:30 | |
| Tue., 4/9 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:30 p.m. | PU 3:00 RE 5:00 | |
| Tue., 4/9 | V Boys Lacrosse | Darien | Home - Taft Field [Directions] | L 7-24 | ||
| Tue., 4/9 | JV Boys Lacrosse | Darien | Home - Tomlinson MS [Directions] | Cancelled | ||
| Tue., 4/9 | FR Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Tue., 4/9 | V Boys Outdoor Track | St. Joseph, Darien | Away [Directions] | 4:00 p.m. | PU 2:45 RE 5:30 | |
| Tue., 4/9 | V Girls Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 199 New Canaan: 173 | ||
| Tue., 4/9 | JV Girls Golf | New Canaan | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Darien | Home - Taft Field [Directions] | L 8-18 | ||
| Tue., 4/9 | JV Girls Lacrosse | Darien | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | FR Girls Lacrosse | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Tue., 4/9 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 4/10 | V Baseball | Brien McMahon | Home - Kiwanis Field [Directions] | W 2-0 | ||
| Wed., 4/10 | JV Baseball | Brien McMahon | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Wed., 4/10 | V Boys Golf | Westhill | Home - Smith Richardson Golf Course [Directions] | Ludlowe 175/ Westhill 195 | ||
| Wed., 4/10 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | L 1-6 | PU 2:30 RE 5:30 | |
| Wed., 4/10 | JV Boys Tennis | Greenwich | Home - Tomlinson MS Tennis Courts [Directions] | 4:30 p.m. | Ride with varsity | |
| Wed., 4/10 | V Boys Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Wed., 4/10 | JV Boys Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/10 | V Co-ed Sailing | Darien | Home - Pequot YC [Directions] | 3:30 p.m. | ||
| Wed., 4/10 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 18-3 | PU 2:30 RE 5:30 | |
| Wed., 4/10 | V Girls Tennis | Ridgefield | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/10 | JV Girls Tennis | Ridgefield | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Lacrosse | Conard | Away - Conard HS Stadium [Directions] | L 8-9(OT) | PU 2:30 RE 6:30 | |
| Thu., 4/11 | JV Boys Lacrosse | Conard | Away - Conard HS North Field [Directions] | 5:00 p.m. | PU 2:30 RE 6:30 | |
| Thu., 4/11 | V Boys Tennis | Trumbull | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/11 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Thu., 4/11 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | Ludlowe: 180 Danbury: 227 | PU 1:50 RE 5:30 | |
| Thu., 4/11 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:45 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 13-6 | PU 2:30 RE 7:15 | |
| Thu., 4/11 | JV Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Thu., 4/11 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:00 | |
| Thu., 4/11 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 5-1 | PU 2:15 RE 5:30 | |
| Thu., 4/11 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 5-2 | PU 2:30 RE 5:30 | |
| Thu., 4/11 | JV Girls Tennis | Darien | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Baseball | Stamford | Away - SHS Baseball Field [Directions] | W 4-0 | PU 2:30 RE 5:30 | |
| Fri., 4/12 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Fri., 4/12 | FR Baseball | Stamford | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Staples | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Fri., 4/12 | JV Boys Volleyball | Staples | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Softball | Stamford | Home - Sturges Park [Directions] | W 3-2 | ||
| Fri., 4/12 | JV Softball | Stamford | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Mt. Greylock (MA) | Away | W 20-6 | PU 9:00 RE 4:00 | |
| Sat., 4/13 | JV Boys Lacrosse | Mt. Greylock (MA) | Away | Cancelled | ||
| Sat., 4/13 | V Co-ed Sailing | O'Day Qualifier | Away - Indian Harbor Yacht Club | TBA | PU 7:45 RE 3:30 | |
| Sat., 4/13 | V Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | W 11-7 | PU 11:30 RE 4:00 | |
| Sat., 4/13 | JV Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 1:00 p.m. | Ride with varsity | |
| Mon., 4/15 | FR Boys Lacrosse | Greenwich | Home - Tomlinson MS [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | W 13-4 | PU 2:30 RE 7:00 | |
| Mon., 4/15 | JV Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | 5:30 p.m. | Ride with varsity | |
| Tue., 4/16 | V Baseball | Greenwich | Away - Julian Curtiss School [Directions] | W 4-2 | PU 9:30 RE 2:30 | |
| Tue., 4/16 | V Baseball | Greenwich | Away - Julian Curtiss School [Directions] | W 6-1 | See above | |
| Tue., 4/16 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Tue., 4/16 | FR Baseball | Greenwich | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Middletown | Away - Wilson Middle 370 Hunting Hill Ave. [Directions] | W 24-1 | PU 3:00 RE 6:30 | |
| Tue., 4/16 | V Boys Tennis | Trinity Catholic | Away | W 7-0 | PU 9:00 RE 12:00 | |
| Tue., 4/16 | V Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | W 15-10 | ||
| Tue., 4/16 | JV Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | 1:30 p.m. | ||
| Tue., 4/16 | V Softball | Greenwich | Home - Dougiello Field [Directions] | W 9-2 | ||
| Tue., 4/16 | V Girls Tennis | Trinity Catholic | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/17 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 2-1 | PU 2:30 RE 5:30 | |
| Wed., 4/17 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 4/17 | FR Baseball | Ridgefield | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Trumbull | Home - Tomlinson MS [Directions] | Cancelled | ||
| Wed., 4/17 | V Boys Tennis | Fairfield Prep | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 2-5 | ||
| Wed., 4/17 | V Softball | Ridgefield | Home - Dougiello Field [Directions] | W 9-2 | ||
| Wed., 4/17 | JV Softball | Ridgefield | Home - Dougiello Field [Directions] | 3:15 p.m. | ||
| Thu., 4/18 | V Baseball | Trumbull | Home - Kiwanis Field [Directions] | W 6-5 (8) | ||
| Thu., 4/18 | JV Baseball | Trumbull | Home - Tunxis Hill Park [Directions] | 10:00 a.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Brien McMahon | Home - Taft Field [Directions] | W 15-6 | ||
| Thu., 4/18 | JV Boys Lacrosse | Brien McMahon | Home - Taft Field [Directions] | 2:00 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | W 3-2 | PU 2:30 RE 6:30 | |
| Mon., 4/22 | JV Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:30 p.m. | Ride with JV | |
| Tue., 4/23 | V Boys Tennis | Bridgeport Central | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/23 | V Girls Golf | St. Joseph | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 196 St. Joes: 223 | ||
| Tue., 4/23 | V Girls Lacrosse | Danbury | Home - Taft Field [Directions] | W 18-1 | ||
| Tue., 4/23 | JV Girls Lacrosse | Danbury | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | PU 2:30 RE 5:15 | |
| Tue., 4/23 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 4-0 | PU 2:30 RE 5:30 | |
| Tue., 4/23 | V Girls Tennis | Bridgeport Central | Away [Directions] | W 7-0 | PU 2:45 RE 5:00 | |
| Wed., 4/24 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | W 12-3 | PU 2:30 RE RE 5:45 | |
| Wed., 4/24 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Wed., 4/24 | V Boys Outdoor Track | Danbury | Home - Fairfield Ludlowe HS [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 0-7 | PU 2:30 RE 5:30 | |
| Wed., 4/24 | JV Boys Tennis | Greenwich | Home - Tomlinson MS Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | V Boys Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Wed., 4/24 | JV Boys Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | V Co-ed Sailing | Fairfield Prep | Home - Pequot YC [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | FR Girls Lacrosse | Wilton | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Outdoor Track | Danbury | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Wed., 4/24 | V Softball | Trinity Catholic | Home - Sturges Park [Directions] | W 20-0 | ||
| Wed., 4/24 | V Girls Tennis | New Canaan | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | ||
| Wed., 4/24 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Thu., 4/25 | V Baseball | New Canaan | Away - Mead Park [Directions] | W 8-2 | PU 2:30 RE 5:30 | |
| Thu., 4/25 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Thu., 4/25 | FR Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Thu., 4/25 | V Boys Golf | Darien | Away - Woodway CC [Directions] | Ludlowe 170/ Darien 160 | PU 2:00 RE 5:30 | |
| Thu., 4/25 | V Boys Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | ||
| Thu., 4/25 | JV Boys Tennis | Darien | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Girls Golf | Darien | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | L 4-14 | PU 2:30 RE 6:30 | |
| Thu., 4/25 | JV Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 5:30 p.m. | Ride with varsity | |
| Thu., 4/25 | V Softball | Harding | Away - Luis Marin #1 [Directions] | W 14-0 | Ride with Fr Base/JV SB, Seperate RE | |
| Thu., 4/25 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:15 p.m. | Ride with Fr Baseball | |
| Thu., 4/25 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 2-5 | PU 2:00 RE 5:30 | |
| Thu., 4/25 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | Ride with varsity/ Golf | |
| Fri., 4/26 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 0-3 | PU 2:30 RE 7:00 | |
| Fri., 4/26 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | Ride with varsity | |
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Bethel H.S. | 9:00 a.m. | PU 7:15 RE 2:30 | |
| Sat., 4/27 | V Co-ed Sailing | Connecticut State Sailing Championship | Away - Captain's Cove | TBA | No bus | |
| Sat., 4/27 | V Girls Lacrosse | Ridgefield | Home - Taft Field [Directions] | L 6-11 | ||
| Sat., 4/27 | JV Girls Lacrosse | Ridgefield | Home - Taft Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away - Bethel H.S. | 9:00 a.m. | PU 7:15 RE 2:30 | |
| Sun., 4/28 | V Co-ed Sailing | Herreshoff | Away - Black Rock Harbor | TBA | No Bus | |
| Mon., 4/29 | V Baseball | Bridgeport Central | Home - Kiwanis Field [Directions] | W 8-0 | ||
| Mon., 4/29 | V Boys Golf | Staples | Home - Smith Richardson Golf Course [Directions] | Ludlowe 173/ Staples 173 | ||
| Mon., 4/29 | JV Boys Golf | Staples | Home - Smith Richardson Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 4/29 | V Boys Outdoor Track | Norwalk, Wilton | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Tennis | St. Joseph | Away [Directions] | W 6-1 | PU 2:30 RE 5:30 | |
| Mon., 4/29 | JV Boys Tennis | Trumbull | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Mon., 4/29 | JV Boys Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Girls Golf | Ridgefield | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 187 Ridgefield: 189 | ||
| Mon., 4/29 | FR Girls Lacrosse | Darien | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Norwalk, Wilton | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 26-0 | PU 2:45 RE 5:30 | |
| Mon., 4/29 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Mon., 4/29 | V Girls Tennis | St. Joseph | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Tue., 4/30 | V Boys Golf | Brien McMahon | Home - Smith Richardson Golf Course [Directions] | Ludlowe 160/Brien McMahon 210 | ||
| Tue., 4/30 | V Boys Lacrosse | New Canaan | Home - Taft Field [Directions] | L 6-15 | ||
| Tue., 4/30 | JV Boys Lacrosse | New Canaan | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Westhill | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 2-4 | ||
| Tue., 4/30 | JV Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 5:30 p.m. | PU 4:00 RE 7:00 | |
| Tue., 4/30 | JV Girls Golf | New Canaan | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 4/30 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 21-6 | PU 3:15 RE 8:00 | |
| Tue., 4/30 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | Ride with varsity | |
| Tue., 4/30 | V Softball | New Canaan | Home - Sturges Park [Directions] | W 3-0 | ||
| Tue., 4/30 | V Girls Tennis | Westhill | Away [Directions] | W 4-3 | PU 2:30 RE 5:30 | |
| Wed., 5/1 | V Baseball | Darien | Home - Kiwanis Field [Directions] | W 4-1 | ||
| Wed., 5/1 | JV Baseball | Darien | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Wed., 5/1 | V Boys Golf | Trumbull | Home - Smith Richardson Golf Course [Directions] | Ludlowe 159/ Trumbull 157 | ||
| Wed., 5/1 | JV Boys Golf | Trumbull | Home - Smith Richardson Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/1 | V Boys Volleyball | Danbury | Home - FLHS Main Gym [Directions] | L 0-3 | ||
| Wed., 5/1 | JV Boys Volleyball | Danbury | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/1 | V Co-ed Sailing | Fairfield Prep | Home - Pequot YC [Directions] | 3:30 p.m. | ||
| Wed., 5/1 | V Girls Golf | Staples | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 200 Staples: 190 | ||
| Wed., 5/1 | FR Girls Lacrosse | Norwalk | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | W 12-0 | PU 2:30 RE 5:30 | |
| Wed., 5/1 | JV Girls Tennis | Lauralton Hall | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | L 8-3 | PU 2:30 RE 5:30 | |
| Thu., 5/2 | JV Baseball | St. Joseph | Away - Unity Park, Trumbull [Directions] | 3:30 p.m. | Ride with varsity | |
| Thu., 5/2 | FR Baseball | St. Joseph | Home - Kiwanis Field [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | JV Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | 3:30 p.m. | PU 2:30 RE 5:00 | |
| Thu., 5/2 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 10-12 | PU 3:45 RE 6:30 | |
| Thu., 5/2 | V Boys Tennis | Staples | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Thu., 5/2 | JV Boys Tennis | Staples | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | Ludlowe: 189 Wilton: 187 | PU 2:30 RE 4:30 | |
| Thu., 5/2 | JV Girls Golf | Staples | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 9-3 | PU 5:15 RE NO | |
| Thu., 5/2 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | PU 2:45 RE NO | |
| Thu., 5/2 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 1-6 | PU 2:45 RE 5:30 | |
| Thu., 5/2 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | Ride with varsity | |
| Thu., 5/2 | Miscellaneous Events | Middle School Track Meet | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Staples | Home - Tomlinson MS [Directions] | Cancelled | ||
| Fri., 5/3 | V Boys Outdoor Track | Middletown Invitational | Away | Cancelled | ||
| Fri., 5/3 | V Boys Volleyball | Westhill | Home - FLHS Main Gym [Directions] | W 3-1 | ||
| Fri., 5/3 | JV Boys Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | Middletown Invitational | Away | Cancelled | ||
| Fri., 5/3 | V Softball | St. Joseph | Home - Sturges Park [Directions] | L 11-0 | ||
| Fri., 5/3 | JV Softball | St. Joseph | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | JV Baseball | Danbury | Home - Kiwanis Field [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | L 6-12 | PU 3:45 RE 6:30 | |
| Sat., 5/4 | JV Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | Cancelled | ||
| Sat., 5/4 | FR Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 10:00 a.m. | No Bus | |
| Sat., 5/4 | V Boys Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | PU 11:00 RE 5:30 | |
| Sat., 5/4 | V Girls Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | W 13-12 | PU 12:15 RE 5:00 | |
| Sat., 5/4 | JV Girls Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 2:00 p.m. | Ride with varsity | |
| Sat., 5/4 | V Girls Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | Ride with boys track (One Bus) | |
| Mon., 5/6 | JV Boys Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | V Boys Lacrosse | Norwalk | Home - Taft Field [Directions] | W 13-3 | ||
| Mon., 5/6 | JV Boys Lacrosse | Norwalk | Home - Taft Field [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Darien | Home - Tomlinson MS [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Fairfield Warde | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/6 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | PU 2:45 RE 5:30 | |
| Mon., 5/6 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 1-3 | PU 2:30 RE 7:00 | |
| Mon., 5/6 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | Ride with varsity | |
| Mon., 5/6 | V Girls Golf | Greenwich | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 182 Greenwich: 191 | ||
| Mon., 5/6 | V Girls Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 182 Warde: 177 | ||
| Mon., 5/6 | FR Girls Lacrosse | Greenwich | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Westhill | Away - Westhill Softball Field [Directions] | W 15-2 | PU 2:20 RE 5:30 | |
| Mon., 5/6 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | Ride with varsity | |
| Mon., 5/6 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 5-2 | PU 2:45 RE NO | |
| Mon., 5/6 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | Ride with varsity | |
| Tue., 5/7 | V Baseball | Westhill | Home - Kiwanis Field [Directions] | W 14-4 (6) | ||
| Tue., 5/7 | JV Baseball | Westhill | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | PU: 2:30 RE 5:30 | |
| Tue., 5/7 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | Ludlowe 163/Stamford 203 | PU 2:00 RE 5:30 | 1:45 Early Dismissal |
| Tue., 5/7 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | L 6-8 | PU 3:00 RE 6:00 | |
| Tue., 5/7 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 6:00 p.m. | PU 4:30 RE 7:15 | |
| Tue., 5/7 | V Boys Outdoor Track | New Canaan, Brien McMahon | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | W 5-2 | PU 2:30 RE 5:30 | |
| Tue., 5/7 | JV Girls Golf | Staples | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | New Canaan, Brien McMahon | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Norwalk | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Wed., 5/8 | V Baseball | Staples | Home - Kiwanis Field [Directions] | W 14-0 (5) | ||
| Wed., 5/8 | JV Baseball | Staples | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | PU 2:45 RE 5:30 | |
| Wed., 5/8 | V Boys Golf | Greenwich | Away - Round Hill Country Club [Directions] | Ludlowe 167/ Greenwich 155 | PU 2:00 RE 5:30 | 1:45 Early Dismissal |
| Wed., 5/8 | FR Boys Lacrosse | Westhill | Home - Tomlinson MS [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | New Canaan | Home - FLHS Aux Gym [Directions] | L 0-3 | ||
| Wed., 5/8 | JV Boys Volleyball | New Canaan | Home - FLHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Co-ed Sailing | Greenwich | Away [Directions] | 3:30 p.m. | PU 2:25 RE 5:30 | |
| Wed., 5/8 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Ludlowe: 183 Greenwich: 192 | Ride with boys golf | 1:45 Early Dismissal |
| Wed., 5/8 | V Girls Lacrosse | Wilton | Home - Taft Field [Directions] | W 9-6 | ||
| Wed., 5/8 | FR Girls Lacrosse | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Staples | Away - Wakeman Field [Directions] | W 9-3 | PU 2:45 RE 5:30 | |
| Wed., 5/8 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 5/8 | JV Girls Tennis | New Canaan | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | PU 2:30 NO RE (Owen Fish Shuttle) | |
| Thu., 5/9 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Ludlowe 172/ New Canaan 166 | PU 2:00 RE 5:15 | 1:45 Early Dismissal |
| Thu., 5/9 | V Boys Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | W 20-4 | PU 5:15 RE:8:30 | |
| Thu., 5/9 | JV Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | PU 3:15 RE 6:15 | |
| Thu., 5/9 | V Boys Outdoor Track | Loucks Games | Away | 4:30 p.m. | No Bus | |
| Thu., 5/9 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 2-5 | PU 2:30 RE 5:30 | |
| Thu., 5/9 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | Ride with varsity | |
| Thu., 5/9 | V Girls Golf | Staples | Away - Longshore [Directions] | Ludlowe: 192 Staples: 187 | PU 2:15 RE 4:45 | |
| Thu., 5/9 | JV Girls Golf | Ridgefield | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 5/9 | V Girls Outdoor Track | Loucks Games | Away | 4:30 p.m. | No Bus | |
| Thu., 5/9 | V Girls Tennis | Wilton | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Thu., 5/9 | JV Girls Tennis | Wilton | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | L 8-0 | ||
| Fri., 5/10 | V Boys Outdoor Track | Loucks Games | Away | 4:00 p.m. | No Bus | |
| Fri., 5/10 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | PU 2:30 RE 7:00 | |
| Fri., 5/10 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | Ride with varsity | |
| Fri., 5/10 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | PU 4:30 RE 7:00 | |
| Fri., 5/10 | V Girls Outdoor Track | Loucks Games | Away | 4:00 p.m. | No Bus | |
| Fri., 5/10 | V Softball | Fairfield Warde | Away - Dougiello Field [Directions] | L 3-0 | PU 3:30 RE NO | |
| Sat., 5/11 | JV Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | L 5-10 | PU 5:15 RE 8:30 | |
| Sat., 5/11 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | PU 3:00 RE 5:45 | |
| Sat., 5/11 | V Boys Outdoor Track | Law H.S. Froshmore Invitational | Away | 9:00 a.m. | Ride with girls track | |
| Sat., 5/11 | V Boys Outdoor Track | Greater Hartford Invitational | Away - East Hartford H.S. | Cancelled | ||
| Sat., 5/11 | V Boys Outdoor Track | Loucks Games | Away | 9:00 a.m. | No Bus | |
| Sat., 5/11 | V Girls Lacrosse | Staples | Home - Taft Field [Directions] | L 10-11 | ||
| Sat., 5/11 | JV Girls Lacrosse | Staples | Home - Taft Field [Directions] | 5:15 p.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Loucks Games | Away | 9:00 a.m. | No Bus | |
| Sat., 5/11 | V Girls Outdoor Track | Law H.S. Froshmore Invitational | Away | 9:00 a.m. | PU 7:45 RE 1:30 | |
| Sat., 5/11 | V Girls Outdoor Track | Greater Hartford Invitational | Away - East Hartford H.S. | Cancelled | ||
| Sat., 5/11 | JV Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 10:00 a.m. | No bus | |
| Mon., 5/13 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 1-3 | PU 2:30 RE 7:00 | |
| Mon., 5/13 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | Ride with varsity | |
| Tue., 5/14 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | L 11-1 (6) | PU 4:30 RE 7:30 | |
| Tue., 5/14 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | |
| Tue., 5/14 | FR Baseball | Norwalk | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | Ludlowe 154/ Norwalk 205 | PU 2:15 RE 5:30 | |
| Tue., 5/14 | JV Boys Golf | Brien McMahon | Home - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Ridgefield | Home - Taft Field [Directions] | L 2-14 | ||
| Tue., 5/14 | JV Boys Lacrosse | Ridgefield | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 5/14 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | Cancelled | ||
| Tue., 5/14 | V Softball | Norwalk | Home - Dougiello Field [Directions] | W 5-0 | ||
| Tue., 5/14 | V Girls Tennis | Wilton | Away [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | FCIAC Quarterfinals |
| Tue., 5/14 | JV Girls Tennis | Staples | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | W 7-4 | PU 2:30 RE 5:30 | |
| Wed., 5/15 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 5/15 | FR Baseball | Wilton | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Boys Golf | Darien | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 5/15 | V Boys Lacrosse | Immaculate | Home - Taft Field [Directions] | W 19-3 | ||
| Wed., 5/15 | FR Boys Lacrosse | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 4:00 p.m. | No bus | |
| Wed., 5/15 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:15 p.m. | PU 2:15 RE 6:00 | 2 busses |
| Wed., 5/15 | V Boys Tennis | Staples | Away - Staples HS [Directions] | 4:00 p.m. | PU 2:45 RE 5:30 | FCIAC Quarterfinals |
| Wed., 5/15 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 1-3 | PU 2:30 RE 7:00 | |
| Wed., 5/15 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | Ride with varsity | |
| Wed., 5/15 | V Co-ed Sailing | Gold Cup | Away - Grass Island | 3:30 p.m. | PU 2:25 RE 5:30 | Greenwich Academy and Brunswick School |
| Wed., 5/15 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Ludlowe: 188 Warde: 177 | Shuttle | |
| Wed., 5/15 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:15 p.m. | PU 2:15 RE 6:00 | 2 busses |
| Wed., 5/15 | V Softball | Wilton | Home - Sturges Park [Directions] | W 13-3 | ||
| Wed., 5/15 | Miscellaneous Events | Unified Track Meet | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Thu., 5/16 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Ludlowe 160/Ridgefield 164 | PU 1:15 RE 5:30 | 1:00 Early Dismissal |
| Thu., 5/16 | JV Boys Lacrosse | Trinity Catholic | Home - Taft Field [Directions] | Cancelled | ||
| Thu., 5/16 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Ludlowe: 201 Trumbull: 197 | PU 2:20 RE 4:45 | |
| Thu., 5/16 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Ride with varsity | |
| Thu., 5/16 | FR Girls Lacrosse | Ridgefield | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Softball | Naugatuck | Away - Naugatuck HS [Directions] | W 10-7 | PU 2:30 RE 6:00 | |
| Thu., 5/16 | JV Girls Tennis | New Canaan | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Boys Outdoor Track | Danbury Dream Invitational | Away - New Milford H.S. | 7:30 p.m. | No Bus | |
| Fri., 5/17 | V Boys Volleyball | Wolcott Tech | Home - FLHS Main Gym [Directions] | W 3-2 | ||
| Fri., 5/17 | JV Boys Volleyball | Wolcott Tech | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | L 9-11 | PU 2:45 RE 5:30 | FCIAC Quarterfinals |
| Fri., 5/17 | FR Girls Lacrosse | Trumbull | Away - New Turf Field [Directions] | 4:00 p.m. | PU 2:30 RE 5:15 | |
| Fri., 5/17 | V Girls Outdoor Track | Danbury Dream Invitational | Away - New Milford H.S. | 7:30 p.m. | No Bus | |
| Fri., 5/17 | V Softball | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | FCIAC Quarterfinals | |
| Sat., 5/18 | V Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | W 5-4 (9) | FCIAC Quarterfinals | |
| Mon., 5/20 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | Ludlowe 151/Trinity 248 | PU 2:15 RE 5:30 | |
| Mon., 5/20 | JV Boys Golf | Wilton, Darien | Away - Rolling Hills CC [Directions] | 3:30 p.m. | PU 2:45 RE 5:30 | |
| Mon., 5/20 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | L 0-3 | PU 3:00 RE 7:30 | |
| Mon., 5/20 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:30 p.m. | Ride with varsity | |
| Mon., 5/20 | JV Girls Golf | Darien | Away [Directions] | Cancelled | ||
| Mon., 5/20 | JV Girls Tennis | Trumbull | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Baseball | Darien | Home - Cubeta Stadium [Directions] | 7:30 p.m. | PU 6:00 RE 9:00 | FCIAC Semifinals |
| Tue., 5/21 | V Boys Golf | Fairfield Warde, Fairfield Prep, Notre Dame-Fairfield | Away - The Patterson Club [Directions] | Ludlowe 173/ Warde 169 | No Bus | Fairfield Cup |
| Tue., 5/21 | JV Boys Golf | Fairfield Warde, Fairfield Prep | Home - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - SCSU | 1:30 p.m. | PU 11:20 RE 6:00 | 11:05 Early Dismissal |
| Tue., 5/21 | V Girls Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 192 Wilton: 215 | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - SCSU | 1:30 p.m. | PU 11:20 RE 6:00 | 11:05 Early Dismissal |
| Wed., 5/22 | V Baseball | Staples | Away - Cubeta Stadium [Directions] | 7:00 p.m. | PU 5:30 RE 8:30 | FCIAC Championship |
| Wed., 5/22 | V Boys Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | Ludlowe 169/Wilton 168 | ||
| Wed., 5/22 | JV Boys Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | 3:45 p.m. | ||
| Wed., 5/22 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Ludlowe: 209 New Canaan: 187 | PU 2:20 RE 5:15 | |
| Wed., 5/22 | JV Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Ride with varsity | |
| Wed., 5/22 | V Girls Tennis | Pomperaug | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/23 | V Boys Golf | CHAPPA | Away - Longshore CC | TBA | No bus | |
| Thu., 5/23 | V Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | W 3-1 | PU 2:30 RE 7:00 | |
| Thu., 5/23 | JV Boys Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:30 p.m. | Ride with Varsity | |
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - Hall HS [Directions] | 8:30 a.m. | PU 6:30 RE 5:00 (W/Warde) | |
| Sat., 5/25 | V Boys Lacrosse | West Haven | Away [Directions] | 10:00 a.m. | PU 8:15 RE 11:30 | Class L Qualifying Round |
| Sat., 5/25 | V Boys Outdoor Track | Froshmore Championship | Away - Southington H.S. | Cancelled | ||
| Sat., 5/25 | V Boys Tennis | CIAC Tourney Through Quarterfinals | Away - Hall HS [Directions] | TBA | ||
| Sat., 5/25 | V Co-ed Sailing | Baker Cup | Home - Pequot YC [Directions] | TBA | FCSL Schools | |
| Sat., 5/25 | V Girls Outdoor Track | Froshmore Championship | Away - Southington H.S. | Cancelled | ||
| Tue., 5/28 | V Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | 3:30 p.m. | Class LL First Round | |
| Tue., 5/28 | V Boys Golf | HOLOHAN | Away - Woodway CC | TBA | No Bus | |
| Tue., 5/28 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | 4:00 p.m. | No Bus | |
| Tue., 5/28 | V Girls Lacrosse | Conard | Home - Taft Field [Directions] | W 19-9 | Class L First Round | |
| Wed., 5/29 | V Boys Lacrosse | Simsbury | Away - Simsbury HS - Holden Field (turf) [Directions] | 5:30 p.m. | PU 2:45 RE 7:00 (2) | Class L First Round |
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | No Bus | |
| Wed., 5/29 | JV Girls Golf | JV Championship | Home - South Pine Creek Par 3 [Directions] | TBA | ||
| Wed., 5/29 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | PU 12:30 RE 8:00 | 12:15 Early Dismissal |
| Wed., 5/29 | V Softball | Norwalk | Home - Sturges Park [Directions] | W 10-5 | Class LL First Round | |
| Thu., 5/30 | V Baseball | Simsbury | Home - Kiwanis Field [Directions] | 3:00 p.m. | Class LL 2nd Round | |
| Thu., 5/30 | V Boys Golf | FCIAC | Away | TBA | No Bus | |
| Thu., 5/30 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 3:00 p.m. | PU 12:30 RE 8:00 | 12:15 Early Dismissal |
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | 4:00 p.m. | No Bus | |
| Thu., 5/30 | V Girls Lacrosse | Darien | Away - Darien HS [Directions] | 4:00 p.m. | PU 2:30 RE 5:30 | Class L Quarterfinals |
| Thu., 5/30 | V Softball | Norwich Free Academy | Away [Directions] | 4:00 p.m. | PU 1:00 RE 5:30 | 12:45 Early Dismissal |
| Sat., 6/1 | V Baseball | Southington | Away [Directions] | 2:00 p.m. | PU 12:00 RE 3:30 | Class LL Quarterfinals |
| Sat., 6/1 | V Boys Lacrosse | Darien | Away - Darien HS [Directions] | 3:00 p.m. | PU 1:30 RE 4:30 | Class L Quarterfinals |
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 12:00 p.m. | ||
| Mon., 6/3 | V Boys Golf | CIAC | Away - Stanley Golf Course | TBA | PU 6:00 RE 1:00 | |
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | PU 11:30 RE 6:00 | 11:15 Early Dismissal |
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | Ride with boys track | 11:15 Early Dismissal |
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | PU 7:15 RE :1:30 | |
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | No Bus | |
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | TBA | |
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | No Bus | |
| Sun., 6/9 | V Boys Golf | Open Championship | Away - Black Hall Club | TBA | TBA | |
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | TBA | |
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | TBA | |
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | TBA | |
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | TBA | |
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | No Bus | |
| Thu., 6/20 | V Boys Golf | New England Individual | Away - Brentwood Golf Club | TBA | ||