| Fairfield Ludlowe 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 882 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | FR Boys Lacrosse | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| TBA | V Boys Swimming and Diving | New Canaan | Away [Directions] | 3:00 p.m. | ||
| TBA | JV Boys Tennis | Fairfield Warde | Home - Dwight Elementary School Courts [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | New Canaan | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods Middle School Courts [Directions] | 3:45 p.m. | Shuttle Bus - No Return | |
| Wed., 8/28 | V Football | Jonathan Law (Scrim.) | Away [Directions] | 3:45 p.m. | ||
| Thu., 8/29 | V Boys Soccer | Fairfield Prep (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Thu., 8/29 | V Boys Soccer | New Milford (Scrim.) | Home - Taft Field [Directions] | 7:00 p.m. | ||
| Sat., 8/31 | V Football | Fairfield Prep (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 8/31 | V Field Hockey | Norwalk (Scrim.) | Away [Directions] | 11:00 a.m. | ||
| Sat., 8/31 | V Girls Soccer | Shelton (Scrim.) | Away [Directions] | 8:30 a.m. | ||
| Tue., 9/3 | V Girls Volleyball | Bunnell (Scrim.) | Home - FLHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/6 | V Football | Platt Tech (Scrim.) | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Fri., 9/6 | V Boys Soccer | Masuk (Scrim.) | Away - Masuk Middle Field [Directions] | 3:45 p.m. | ||
| Mon., 9/9 | V Field Hockey | Bethel (Scrim.) | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Wilton, St. Joseph, Fairfield Warde | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | L 1-2 | |
| Tue., 9/10 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | JV Travels With Varsity | |
| Tue., 9/10 | FR Boys Soccer | Greenwich | Home - RLMS [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Wilton, St. Joseph, Fairfield Warde | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/11 | V Field Hockey | Wilton | Home - Taft Field [Directions] | 7:00 p.m. | L 0-5 | |
| Wed., 9/11 | JV Field Hockey | Wilton | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | L 2-4 | |
| Wed., 9/11 | JV Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Wed., 9/11 | FR Girls Soccer | Trumbull | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Sideline Cheerleading | Lyman Hall | Away [Directions] | 6:00 p.m. | ||
| Thu., 9/12 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 9/12 | JV Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Thu., 9/12 | FR Girls Soccer | Wilton | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/12 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Sun., 9/15 | V Football | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | 3:00 p.m. | W 24-21 | |
| Mon., 9/16 | JV Football | Danbury | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Boys Soccer | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | W 1-0 | |
| Mon., 9/16 | JV Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | FR Boys Soccer | New Canaan | Home - RLMS [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:15 p.m. | W 1-0 | |
| Mon., 9/16 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Mon., 9/16 | FR Field Hockey | Amistad | Home - Taft Field [Directions] | 6:00 p.m. | Cancelled | |
| Mon., 9/16 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Brien McMahon | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/16 | JV Girls Volleyball | Brien McMahon | Home - FLHS Main Gym [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Mon., 9/16 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 9/17 | V Boys Cross Country | Ridgefield, Darien, Trumbull, Harding | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Ridgefield, Darien, Trumbull, Harding | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Soccer | St. Joseph | Home - Taft Field [Directions] | 6:00 p.m. | L 0-4 | |
| Tue., 9/17 | JV Girls Soccer | St. Joseph | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Boys Soccer | Trinity Catholic | Home - Taft Field [Directions] | 6:00 p.m. | W 5-0 | |
| Wed., 9/18 | FR Field Hockey | Wilton | Away - Wilton High School - Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Bassick | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/18 | JV Girls Volleyball | Bassick | Home - FLHS Main Gym [Directions] | 4:30 p.m. | JV Travels With Varsity | |
| Thu., 9/19 | FR Football | Ridgefield | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 9/19 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/19 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Thu., 9/19 | FR Field Hockey | Westhill | Home [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 9/19 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Thu., 9/19 | FR Girls Soccer | Staples | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 20-41 | |
| Fri., 9/20 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/20 | JV Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Fri., 9/20 | FR Boys Soccer | Darien | Home - RLMS [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Sideline Cheerleading | Ridgefield | Away [Directions] | 7:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/20 | JV Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Fri., 9/20 | FR Girls Volleyball | Wilton | Home [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Girls Soccer | Ridgefield | Home - Taft Field [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 9/21 | JV Girls Soccer | Ridgefield | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 11:00 a.m. | ||
| Mon., 9/23 | JV Football | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Mon., 9/23 | V Boys Soccer | Ridgefield | Home - Taft Field [Directions] | 7:00 p.m. | W 3-1 | |
| Mon., 9/23 | JV Boys Soccer | Ridgefield | Home - RLMS [Directions] | 5:00 p.m. | ||
| Mon., 9/23 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Field Hockey | Danbury | Home - Taft Field [Directions] | 5:15 p.m. | W 4-1 | |
| Mon., 9/23 | JV Field Hockey | Danbury | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Mon., 9/23 | FR Field Hockey | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/23 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Mon., 9/23 | FR Girls Volleyball | Trumbull | Home [Directions] | 5:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Westhill, Greenwich, New Canaan, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Westhill, Greenwich, New Canaan, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 6:30 p.m. | W 5-0 | |
| Wed., 9/25 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 6:00 p.m. | W 1-0 | |
| Wed., 9/25 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | JV Shuttles with Varsity | |
| Wed., 9/25 | FR Boys Soccer | Bridgeport Central | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Field Hockey | Weston | Home - Taft Field [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 9/25 | V Girls Swimming and Diving | St. Joseph | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/25 | V Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | 5:30 p.m. | L 3-1 | |
| Wed., 9/25 | JV Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 9/25 | FR Girls Volleyball | Darien | Away [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Field Hockey | Trumbull | Home - Taft Field [Directions] | 7:00 p.m. | W 3-2 | |
| Thu., 9/26 | JV Field Hockey | Trumbull | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 9/26 | FR Field Hockey | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 9/26 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Fri., 9/27 | V Football | Bridgeport Central | Home - Taft Field [Directions] | 7:00 p.m. | W 46-20 | |
| Fri., 9/27 | V Boys Soccer | Trumbull | Home - Taft Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 9/27 | JV Boys Soccer | Trumbull | Home - RLMS [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | FR Boys Soccer | Trumbull | Away - JV Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Volleyball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/27 | JV Girls Volleyball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/28 | JV Football | Bridgeport Central | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Mon., 9/30 | V Girls Soccer | Greenwich | Home - Taft Field [Directions] | 6:00 p.m. | W 2-0 | |
| Mon., 9/30 | JV Girls Soccer | Greenwich | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Danbury, Bassick, Norwalk | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Harding | Home - Taft Field [Directions] | 6:30 p.m. | W 4-0 | |
| Tue., 10/1 | V Girls Cross Country | Danbury, Bassick, Norwalk | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 0-6 | |
| Tue., 10/1 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Tue., 10/1 | FR Field Hockey | Darien | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | JV Field Hockey | Fairfield Warde | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Wed., 10/2 | V Girls Swimming and Diving | Staples | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/2 | V Girls Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Volleyball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 10/2 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Wilton | Home - Taft Field [Directions] | 4:15 p.m. | L 1-3 | |
| Thu., 10/3 | JV Boys Soccer | Wilton | Home - Sturges Park [Directions] | 4:15 p.m. | ||
| Thu., 10/3 | FR Boys Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Field Hockey | Fairfield Warde | Home - Taft Field [Directions] | 7:00 p.m. | T 1-1 | |
| Thu., 10/3 | V Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/3 | JV Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/3 | FR Girls Volleyball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | FR Field Hockey | Bethel | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Soccer | Fairfield Warde | Home - Taft Field [Directions] | 7:00 p.m. | W 1-0 | |
| Fri., 10/4 | JV Girls Soccer | Fairfield Warde | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Fri., 10/4 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Football | Harding | Home - Taft Field [Directions] | 3:00 p.m. | W 35-31 | |
| Sat., 10/5 | V Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 2:00 p.m. | L 0-1 | |
| Sat., 10/5 | FR Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Mon., 10/7 | JV Football | Harding | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Mon., 10/7 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | Cancelled | JV Travels With Varsity |
| Mon., 10/7 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/7 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Tue., 10/8 | V Boys Cross Country | Staples, Brien McMahon, Stamford, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Staples, Brien McMahon, Stamford, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | OT-L 1-2 | |
| Tue., 10/8 | V Girls Soccer | Bridgeport Central | Home - Taft Field [Directions] | 5:00 p.m. | W 6-0 | |
| Wed., 10/9 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | L 0-1 | |
| Wed., 10/9 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | JV Shuttles with Varsity | |
| Wed., 10/9 | V Girls Volleyball | Norwalk | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/9 | JV Girls Volleyball | Norwalk | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 10/9 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Football | Staples | Away - Wrecker Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/10 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 10/10 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | JV Shuttles with Varsity | |
| Thu., 10/10 | V Field Hockey | Norwalk | Home - Taft Field [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 10/10 | JV Field Hockey | Norwalk | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 10/10 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Thu., 10/10 | FR Girls Soccer | Darien | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Football | Staples | Away - Staples Stadium [Directions] | 7:00 p.m. | L 23-52 | |
| Fri., 10/11 | FR Boys Soccer | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Sideline Cheerleading | Staples | Away [Directions] | 7:00 p.m. | ||
| Fri., 10/11 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/11 | V Girls Volleyball | Harding | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/11 | JV Girls Volleyball | Harding | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/12 | JV Football | Staples | Away - Staples Stadium [Directions] | 10:00 a.m. | ||
| Mon., 10/14 | V Girls Soccer | Westhill | Home - Taft Field [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 10/14 | JV Girls Soccer | Westhill | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/14 | FR Girls Soccer | Fairfield Warde | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Mon., 10/14 | FR Girls Volleyball | New Canaan | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Stamford | Home - Taft Field [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/15 | JV Boys Soccer | Stamford | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Field Hockey | Stamford | Home - Taft Field [Directions] | 4:00 p.m. | W 4-2 | |
| Tue., 10/15 | JV Field Hockey | Stamford | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Wed., 10/16 | V Girls Soccer | Trinity Catholic | Home - Taft Field [Directions] | 6:00 p.m. | W 6-0 | |
| Wed., 10/16 | JV Girls Soccer | Harding | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | FR Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University- Rec Plex Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 10/16 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Wed., 10/16 | FR Girls Volleyball | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Cross Country | FCIAC Championship | Away | 2:50 p.m. | At Waveny Park New Canaan | |
| Thu., 10/17 | FR Football | Norwalk | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Danbury | Home - Taft Field [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 10/17 | JV Boys Soccer | Danbury | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Cross Country | FCIAC Championship | Away | 3:20 p.m. | @ Waveny Park New Canaan | |
| Thu., 10/17 | V Field Hockey | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 10/17 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Thu., 10/17 | FR Field Hockey | Staples | Home [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Soccer | New Canaan | Away - Connor Field [Directions] | 4:00 p.m. | L 1-5 | |
| Fri., 10/18 | JV Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Fri., 10/18 | FR Girls Soccer | New Canaan | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | W 3-2 | |
| Fri., 10/18 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Fri., 10/18 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | ||
| Sat., 10/19 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 3:00 p.m. | W 13-6 | |
| Sat., 10/19 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 2:30 p.m. | W 1-0 | |
| Sat., 10/19 | JV Boys Soccer | St. Joseph | Home - Sturges Park [Directions] | 2:30 p.m. | JV Travels With Varsity | |
| Sat., 10/19 | V Sideline Cheerleading | Norwalk | Away [Directions] | 3:00 p.m. | ||
| Sat., 10/19 | V Field Hockey | Brien McMahon | Home - Taft Field [Directions] | 3:00 p.m. | L 1-2 | |
| Mon., 10/21 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/21 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Mon., 10/21 | FR Boys Soccer | Staples | Home - RLMS [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Field Hockey | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Swimming and Diving | Greenwich | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 10/21 | JV Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | FR Girls Volleyball | Westhill | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 10/22 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Tue., 10/22 | FR Field Hockey | Ridgefield | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Tue., 10/22 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 2-1 | |
| Tue., 10/22 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Tue., 10/22 | FR Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/23 | V Boys Soccer | Norwalk | Home - Taft Field [Directions] | 7:00 p.m. | W 3-2 | |
| Wed., 10/23 | FR Boys Soccer | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Field Hockey | New Canaan | Home - Taft Field [Directions] | 5:00 p.m. | L 1-3 | Senior Night |
| Wed., 10/23 | JV Field Hockey | New Canaan | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Wed., 10/23 | FR Field Hockey | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/23 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | JV Travels With Varsity | |
| Wed., 10/23 | FR Girls Volleyball | Staples | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Danbury | Home - Taft Field [Directions] | 5:00 p.m. | T 0-0 | |
| Thu., 10/24 | JV Girls Soccer | Danbury | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Girls Volleyball | Danbury | Home [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | FR Football | Westhill | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Fri., 10/25 | V Boys Soccer | Stamford | Home - Taft Field [Directions] | 6:30 p.m. | L 0-1 | FCIAC Quarterfinals |
| Fri., 10/25 | FR Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/25 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | JV Travels With Varsity | |
| Sat., 10/26 | V Football | Westhill | Away - Westhill Football Field [Directions] | 2:00 p.m. | L 9-10 | |
| Sat., 10/26 | V Sideline Cheerleading | Westhill | Away [Directions] | 2:00 p.m. | ||
| Sat., 10/26 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 3:30 p.m. | ||
| Mon., 10/28 | JV Football | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/28 | V Girls Swimming and Diving | FCIAC Time Trials | Away | 3:00 p.m. | ||
| Mon., 10/28 | V Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 10/30 | V Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 5:00 p.m. | L 2-3 | FCIAC Semi-Finals |
| Thu., 10/31 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 11/1 | V Football | Brien McMahon | Home - Taft Field [Directions] | 7:00 p.m. | L 9-41 | |
| Sat., 11/2 | JV Football | Brien McMahon | Home - Taft Field [Directions] | 9:30 a.m. | ||
| Mon., 11/4 | V Field Hockey | Hamden | Away [Directions] | 6:00 p.m. | W 2-1 | State Qualifying Round |
| Mon., 11/4 | V Girls Soccer | Amity | Away - Amity High School - Field # 3 [Directions] | 2:00 p.m. | W 2-1 | State 1st Round |
| Tue., 11/5 | V Boys Soccer | Manchester | Home - Taft Field [Directions] | 5:00 p.m. | W 2-0 | State 1st Round |
| Wed., 11/6 | V Field Hockey | Cheshire | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | States 2nd Round | |
| Wed., 11/6 | V Girls Soccer | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | 4:00 p.m. | W 7-5 PK | State 2nd Round |
| Thu., 11/7 | FR Football | East Haven | Away - East Haven High School [Directions] | 4:30 p.m. | ||
| Thu., 11/7 | V Boys Soccer | Danbury | Home - Taft Field [Directions] | 5:00 p.m. | L 0-1 | State 2nd Round |
| Thu., 11/7 | V Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 3-0 | State 2nd Round |
| Fri., 11/8 | V Football | East Haven | Home - Taft Field [Directions] | 7:00 p.m. | W 55-12 | |
| Fri., 11/8 | V Girls Soccer | St. Joseph | Away [Directions] | 2:00 p.m. | State 1/4 Finals | |
| Sat., 11/9 | JV Football | East Haven | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 11/9 | V Girls Swimming and Diving | CIAC LL Trials | Away | 5:00 p.m. | ||
| Sat., 11/9 | V Girls Volleyball | Darien | Away [Directions] | 4:00 p.m. | W 3-2 | State Quarterfinals |
| Tue., 11/12 | V Girls Swimming and Diving | CIAC LL Finals | Away | 6:00 p.m. | ||
| Thu., 11/14 | FR Football | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | V Girls Volleyball | Cheshire | Away - Trumbull High School [Directions] | 7:00 p.m. | State Semi-Finals | |
| Fri., 11/15 | V Football | Stamford | Home - Taft Field [Directions] | 6:00 p.m. | W 42-40 | |
| Mon., 11/18 | JV Football | Fairfield Warde | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 11/21 | FR Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Thu., 11/28 | V Football | Fairfield Warde | Home - Taft Field [Directions] | 10:00 a.m. | L 21-44 | |
| Fri., 11/29 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | TBA | ||
| Sat., 11/30 | V Girls Basketball | Berlin (Scrim.) | Away [Directions] | TBA | ||
| Tue., 12/3 | V Bowling | Kolbe Cathedral | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Thu., 12/5 | V Girls Basketball | Joel Barlow (Scrim.) | Away - Lower Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/7 | V Girls Basketball | Bethel (Scrim.) | Away - Bethel High School [Directions] | 4:30 p.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Rinks at Shelton Preseason | Away | TBA | @ Rinks at Shelton | |
| Sun., 12/8 | V Boys Basketball | Bergen Catholic (NJ) (Scrim.) | Away | 2:00 p.m. | ||
| Mon., 12/9 | Miscellaneous Events | Winter Sports Parents Meeting | - FLHS Main Gym | 7:00 p.m. | ||
| Wed., 12/11 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/11 | V Boys Ice Hockey | Stamford (Scrim.) | Home - Wonderland Of Ice [Directions] | 4:50 p.m. | This scrimmage will be from 4:50 p.m.-5:50 p.m. | |
| Wed., 12/11 | V Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 7:00 p.m. | W 52-48 | |
| Wed., 12/11 | JV Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 12/11 | FR Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Wed., 12/11 | V Girls Ice Hockey | Greenwich | Away [Directions] | 8:30 p.m. | W 4-0 | @ Dorothy Hamill Rink |
| Thu., 12/12 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:00 p.m. | ||
| Fri., 12/13 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 59-23 | |
| Fri., 12/13 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | JV Travels with Varsity | |
| Fri., 12/13 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/13 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Wonderland of Ice [Directions] | 4:40 p.m. | ||
| Sat., 12/14 | V Boys Basketball | Weston (Scrim.) | Home [Directions] | 10:00 a.m. | ||
| Sat., 12/14 | V Boys Ice Hockey | Tournament Game - Opponent Not Known (Scrim.) | Away | 5:45 p.m. | ||
| Mon., 12/16 | V Girls Ice Hockey | North Haven | Home - Wonderland of Ice [Directions] | 5:00 p.m. | ||
| Wed., 12/18 | V Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 63-70 | |
| Wed., 12/18 | JV Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Harding | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Boys Fencing | Cheshire | Away [Directions] | 5:00 p.m. | ||
| Wed., 12/18 | V Boys Ice Hockey | Branford | Home - Wonderland Of Ice [Directions] | 6:30 p.m. | L 2-5 | |
| Wed., 12/18 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | ||
| Wed., 12/18 | V Wrestling | Greens Farms Academy (Scrim.) | Away | 5:00 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:15 p.m. | W 72-44 | |
| Wed., 12/18 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 3:45 p.m. | JV Travels with Varsity | |
| Wed., 12/18 | FR Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Girls Fencing | Cheshire | Away [Directions] | 5:00 p.m. | ||
| Wed., 12/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | 6:00 p.m. | @ Sono Ice Rink | |
| Thu., 12/19 | V Bowling | Platt Tech | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Fri., 12/20 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | W 48-47 | |
| Fri., 12/20 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 12/20 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Darien | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 54-32 | |
| Fri., 12/20 | JV Girls Basketball | Darien | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Girls Basketball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 12:00 p.m. | L 0-2 | Pick up and return to FLHS |
| Sat., 12/21 | V Boys Indoor Track | Staples Developmental Meet | Away | 10:00 a.m. | vs Staples, Darien Greenwich, Warde, St. Joe, McMahon, Stamford | |
| Sat., 12/21 | V Wrestling | Ludlowe Invitational | Home - FLHS Main Gym [Directions] | 9:30 a.m. | [Detailed Results] | McMahon, Cheshire, Staples, Enfield, Windsor, Bethel, Harding, Prep, Central, Newtown, New Britian |
| Sat., 12/21 | V Girls Indoor Track | Staples Developmental Meet | Away | 10:00 a.m. | vs Staples, Darien, Greenwich, Warde, St. Joe, McMahon, Stamford | |
| Thu., 12/26 | V Boys Basketball | Notre Dame-Fairfield | Away - Fairfield University [Directions] | 6:00 p.m. | L 52-56 | |
| Fri., 12/27 | JV Boys Basketball | Notre Dame-Fairfield | Home - FLHS Main Gym [Directions] | 2:00 p.m. | ||
| Fri., 12/27 | V Wrestling | Harding/Bassick/Bridgeport Central | Home - FLHS Aux Gym [Directions] | 5:00 p.m. | Ludlowe 57 Harding 18 | |
| Fri., 12/27 | V Girls Basketball | Brookfield | Home - FLHS Main Gym [Directions] | 6:00 p.m. | W 57-32 | |
| Fri., 12/27 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 10:00 a.m. | ||
| Fri., 12/27 | V Girls Ice Hockey | Greenwich | Home - Wonderland of Ice [Directions] | 4:40 p.m. | ||
| Sat., 12/28 | V Boys Basketball | Fairfield Warde | Away [Directions] | TBA | L 50-60 | |
| Sat., 12/28 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | 8:30 p.m. | L 2-5 | Pick up and return to FLHS |
| Sat., 12/28 | V Wrestling | Danbury Tournament | Away | 9:30 a.m. | ||
| Mon., 12/30 | JV Boys Basketball | Walter Fitzgerald JV Holiday Tourney | Home - FLHS Main Gym [Directions] | TBA | ||
| Mon., 12/30 | V Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 6:00 p.m. | W 51-50 | |
| Thu., 1/2 | JV Boys Fencing | North Haven | Away [Directions] | 6:00 p.m. | ||
| Thu., 1/2 | V Bowling | Fairfield Prep | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Thu., 1/2 | JV Girls Fencing | North Haven | Away [Directions] | 6:00 p.m. | ||
| Sat., 1/4 | JV Boys Fencing | North Haven | Away [Directions] | 9:00 a.m. | ||
| Sat., 1/4 | V Boys Ice Hockey | North Branford | Home - Wonderland Of Ice [Directions] | 8:00 p.m. | L 2-3 | |
| Sat., 1/4 | V Boys Indoor Track | Staples Developmental Meet | Away | 10:00 a.m. | vs Staples, Danbury, Greenwich, Trumbull, New Canaan, McMahon, Westhill | |
| Sat., 1/4 | V Wrestling | Warde Tournament | Away | 9:30 a.m. | RHAM, McMahon, NFA, Wilton, Prep, Westhill, Stamford, Mahopac, New Fairfield, Simsbury, Brookfield, Montville | |
| Sat., 1/4 | JV Girls Fencing | North Haven | Away [Directions] | 9:00 a.m. | ||
| Sat., 1/4 | V Girls Gymnastics | Pompersug Invite | Away | TBA | 131.55 2nd/13 teams | |
| Sat., 1/4 | V Girls Indoor Track | Staples Developmental Meet | Away | 10:00 a.m. | vs Staples, Danbury, Greenwich, Trumbull, New Canaan, McMahon, Westhill | |
| Mon., 1/6 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 54-61 | |
| Mon., 1/6 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Mon., 1/6 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:45 p.m. | Shuttle with varsity bus | |
| Mon., 1/6 | V Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 41-53 | |
| Mon., 1/6 | JV Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/6 | FR Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/6 | V Girls Gymnastics | Staples | Away [Directions] | 6:00 p.m. | Ludlowe- 130.55 Staples- 124.55 | @ Gymnastics and Cheer Academy |
| Tue., 1/7 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 53-65 | |
| Tue., 1/7 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Tue., 1/7 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | V Bowling | Stratford | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 1/7 | V Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 53-47 | |
| Tue., 1/7 | JV Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | St. Joseph | Home - Wonderland Of Ice [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 1/8 | V Wrestling | New Canaan | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | Ludlowe 60 New Canaan 21 | |
| Wed., 1/8 | V Girls Gymnastics | Trumbull | Home - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 6:30 p.m. | Ludlowe- 131.85 Trumbull- 131.95 | @ Gymnastics and Cheer Academy |
| Wed., 1/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Wonderland of Ice [Directions] | 3:45 p.m. | ||
| Thu., 1/9 | V Boys Swimming and Diving | Greenwich, Fairfield Warde | Away - GHS Pool [Directions] | 3:45 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 59-54 | |
| Fri., 1/10 | JV Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | 5:45 p.m. | W 69-34 | |
| Fri., 1/10 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | JV travels with Varsity | |
| Fri., 1/10 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/10 | V Girls Ice Hockey | New Canaan | Home - Wonderland of Ice [Directions] | 4:40 p.m. | ||
| Sat., 1/11 | V Boys Fencing | Greenwich | Home - Fairfield Warde Small Gym [Directions] | 10:00 a.m. | This is a Tri-meet that also includes Guilford High School | |
| Sat., 1/11 | V Boys Ice Hockey | Norwalk | Home - Wonderland Of Ice [Directions] | 8:00 p.m. | W 6-1 | |
| Sat., 1/11 | V Boys Indoor Track | Wilton Developmental Meet | Away | 9:30 a.m. | Wilton, Greenwich, Trumbull Warde, New Canaan, McMahon, Norwalk | |
| Sat., 1/11 | V Wrestling | Farmington Tourney | Away | 9:00 a.m. | ludlowe 51 Wilton 27 Ludlowe 51 Suffield 23 Ludlowe 59 Fitch 9 Ludlowe 27 Farmington 37 | Wilton, Suffield, Fitch, Oxford |
| Sat., 1/11 | V Girls Fencing | Greenwich | Home - Fairfield Warde Small Gym [Directions] | 10:00 a.m. | Will also be competing against Guilford HS in Tri Meet | |
| Sat., 1/11 | V Girls Ice Hockey | Darien | Away [Directions] | 6:00 p.m. | @ Darien Ice Rink | |
| Sat., 1/11 | V Girls Indoor Track | Wilton Developmental Meet | Away | 9:30 a.m. | vs Wilton, Danbury, Greenwich, St. JOe, McMahon, Westhill, Stamford | |
| Tue., 1/14 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 7:00 p.m. | L 48-63 | |
| Tue., 1/14 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Tue., 1/14 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | Frosh shuttle with Var/JV | |
| Tue., 1/14 | V Girls Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 5:30 p.m. | W 72-35 | |
| Tue., 1/14 | JV Girls Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | FR Girls Basketball | Staples | Away - Staples Field House [Directions] | 3:45 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 6:00 p.m. | L 2-6 | Pick up and return to FLHS |
| Wed., 1/15 | V Boys Swimming and Diving | Staples | Away [Directions] | 4:00 p.m. | ||
| Wed., 1/15 | V Wrestling | Derby/Oxford/Holy Cross | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | Ludlowe 31 Derby 30 | |
| Wed., 1/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 3:30 p.m. | @ Ridgefield Ice Rink | |
| Fri., 1/17 | V Boys Basketball | Bassick | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 61-46 | |
| Fri., 1/17 | JV Boys Basketball | Bassick | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Bassick | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 3:30 p.m. | W 60-17 | |
| Fri., 1/17 | JV Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 5:00 p.m. | JV travels with Varsity | |
| Sat., 1/18 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 6:30 p.m. | L 0-1 | Pick up and return to FLHS |
| Sat., 1/18 | V Boys Indoor Track | Wilton Developmental Meet | Away | 9:30 a.m. | vs Wilton, Greenwich, Trumbull Warde, New Canaan, McMahon, Norwalk | |
| Sat., 1/18 | V Wrestling | Ludlowe Legends Duals | Home - FLHS Main Gym [Directions] | 9:00 a.m. | 1st Trumbull 5-0
2nd Ludlowe 4-1
3rd Greenwich 3-2
4th Branford 2-3
5th New Haven 1-4
6th Platt Tech 0-5
Ludlowe 38 Greenwich 30
Ludlowe 58 to Branford 24
Ludlowe 54- New Haven 12
Ludlowe 52 Plat Tech 9
Ludlowe 30 Trumbull 50
Trumbull 68 Platt Tech 9
Trumbull 44 Branford 30
Trumbull 61 New Haven 9
Trumbull 47 Greenwich 27
Branford 52 New Haven 27
Greenwich 64 Platt Tech 0
Branford 56 Platt Tech 15
Greenwich 72 New Haven 12
Greenwich 42 Branford 21
Platt Tech 38 New Haven 42 [Detailed Results] | Trumbull, Branford, Platt Tech, Greenwich, New Haven |
| Sat., 1/18 | V Girls Gymnastics | Darien, Fairfield Warde | Away - DARIEN YMCA [Directions] | 3:30 p.m. | Cancelled | |
| Sat., 1/18 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Wonderland of Ice [Directions] | 1:00 p.m. | ||
| Sat., 1/18 | V Girls Indoor Track | Wilton Developmental Meet | Away | 9:30 a.m. | vs Wilton, Greenwich, Trumbull Warde, New Canaan, McMahon, Norwalk | |
| Mon., 1/20 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 10:30 a.m. | Ludlowe- 134.85 Warde- 130.75 | |
| Mon., 1/20 | V Girls Ice Hockey | Daniel Hand Coop | Away [Directions] | 2:00 p.m. | @ Northford Rink | |
| Tue., 1/21 | V Bowling | St. Joseph | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Wed., 1/22 | V Wrestling | Darien | Away - DHS - South Gym [Directions] | 4:00 p.m. | LUDLOWE 58 DARIEN 10 | |
| Wed., 1/22 | V Girls Ice Hockey | Notre Dame-Fairfield | Away [Directions] | 6:15 p.m. | @ Milford Ice Pavilion | |
| Thu., 1/23 | FR Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 1/23 | V Girls Gymnastics | Wilton | Away - Wilton High School Aux. Gym [Directions] | 4:00 p.m. | Ludlowe- 139.00 Wilton- 139.40 | |
| Sat., 1/25 | V Boys Indoor Track | FCIAC Divisional Championships | Away | 2:00 p.m. | @ Wilton HS | |
| Sat., 1/25 | V Wrestling | East Windsor Rodney Smith Classic | Away | TBA | [Detailed Results] | |
| Sat., 1/25 | V Girls Indoor Track | FCIAC Divisional Championships | Away | 2:00 p.m. | @ Wilton HS | |
| Mon., 1/27 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 7:00 p.m. | W 45-39 | |
| Mon., 1/27 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Mon., 1/27 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | Frosh Shuttle with Var/JV | |
| Mon., 1/27 | V Girls Gymnastics | New Canaan, Westhill | Home - Gymnastics Cheer Academy [Directions] | 6:30 p.m. | Ludlowe- 128.10, Westhill- 98.7, New Canaan- 96.3 | |
| Tue., 1/28 | V Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 45-58 | |
| Tue., 1/28 | JV Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Fencing | Bridgeport Central | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/28 | V Bowling | Joel Barlow | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 1/28 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 70-20 | |
| Tue., 1/28 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | JV travels with Varsity | |
| Tue., 1/28 | V Girls Fencing | Bridgeport Central | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | V Boys Fencing | Cheshire | Home [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | W 5-2 | Pick up and return to FLHS |
| Wed., 1/29 | V Boys Indoor Track | FCIAC Championships | Away | 4:30 p.m. | @ Floyd Little AC New Haven | |
| Wed., 1/29 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | ||
| Wed., 1/29 | V Wrestling | Wilton | Away - Wilton Field House [Directions] | 5:00 p.m. | ||
| Wed., 1/29 | V Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 53-32 | |
| Wed., 1/29 | JV Girls Basketball | Staples | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/29 | V Girls Fencing | Cheshire | Home - Fairfield Warde Small Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Wonderland of Ice [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | V Girls Indoor Track | FCIAC Championships | Away | 4:30 p.m. | @ Floyd Little AC New Haven | |
| Fri., 1/31 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 7:00 p.m. | L 53-57 | |
| Fri., 1/31 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 1/31 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 63-44 | |
| Fri., 1/31 | JV Girls Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/1 | FR Boys Fencing | Novice Tournament @ Guilford HS | Away | 9:00 a.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | Westhill/Stamford | Home - Wonderland Of Ice [Directions] | 8:00 p.m. | W 3-2 (OT) | |
| Sat., 2/1 | V Wrestling | Ludlowe Classic Duals | Home - FLHS Main Gym [Directions] | 9:00 a.m. | [Detailed Results] | Guilford, Norwalk, Immaculate, Barlow, Stratford, Conard |
| Sat., 2/1 | FR Girls Fencing | Novice Tournament @ Guilford HS | Away | 9:00 a.m. | ||
| Sat., 2/1 | V Girls Ice Hockey | New Canaan | Away [Directions] | 8:00 p.m. | @ Darien Ice Rink | |
| Tue., 2/4 | V Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 54-64 | |
| Tue., 2/4 | JV Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Bowling | Bunnell | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 53-63 | |
| Tue., 2/4 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Tue., 2/4 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/5 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 7:30 p.m. | W 4-3 | Pick up and return to FLHS |
| Thu., 2/6 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Wrestling | Ridgefield | Home - FLHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 42-47 | |
| Fri., 2/7 | JV Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Wrestling | Stamford, Brien McMahon, Westhill | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Stamford | Away - Stamford High School [Directions] | 7:00 p.m. | L 47-60 | |
| Fri., 2/7 | JV Girls Basketball | Stamford | Away - Stamford High School [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 2/7 | FR Girls Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 4:00 p.m.p.m. | @ Rinks at Shelton | |
| Sat., 2/8 | V Boys Ice Hockey | Ridgefield | Home - Wonderland Of Ice [Directions] | 8:00 p.m. | L 1-2 | |
| Sat., 2/8 | JV Wrestling | Matt Narwold Ludlowe JV Classic | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/8 | V Girls Ice Hockey | Darien | Home - Wonderland of Ice [Directions] | 3:30 p.m. | ||
| Sat., 2/8 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | ||
| Mon., 2/10 | FR Boys Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 7:45 p.m. | ||
| Mon., 2/10 | V Boys Ice Hockey | Cheshire | Away - Northford Ice rink [Directions] | 4:45 p.m. | L 6-8 | Pick up and return to FLHS |
| Mon., 2/10 | FR Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/10 | V Girls Gymnastics | Foran | Away - Foran High School [Directions] | 6:30 p.m. | Ludlowe- 123.60 Foran- 105.10 | |
| Tue., 2/11 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:45 p.m. | L 46-47 (OT) | |
| Tue., 2/11 | JV Boys Basketball | Fairfield Warde | Home - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Danbury, Fairfield Warde | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | ||
| Tue., 2/11 | V Wrestling | Fairfield Warde | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/11 | V Bowling | Greenwich | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | L 47-52 | Shuttle with JVG & VB |
| Tue., 2/11 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | Shuttle | |
| Tue., 2/11 | V Girls Gymnastics | Greenwich | Home - Gymnastics Cheer Academy [Directions] | 6:30 p.m. | Ludlowe- 125.85 Greenwich- 124.80 | |
| Wed., 2/12 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 5-4 (OT) | Pick up and return to FLHS |
| Wed., 2/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Wonderland of Ice [Directions] | 6:15 p.m. | ||
| Fri., 2/14 | FR Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 2/14 | V Boys Swimming and Diving | Darien | Away - YMCA pool [Directions] | 3:00 p.m. | ||
| Fri., 2/14 | FR Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 2/15 | V Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | 12:00 p.m. | W 51-40 | |
| Sat., 2/15 | JV Boys Basketball | Westhill | Home - FLHS Main Gym [Directions] | 10:15 a.m. | ||
| Sat., 2/15 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC Finals @ New Canaan | Away | 10:00 a.m. | ||
| Sat., 2/15 | V Wrestling | FCIAC Tourney @ New Canaan | Away | 9:00 a.m. | ||
| Sat., 2/15 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | W 54-34 | |
| Sat., 2/15 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championship @ Westhill | Away | 11:00 a.m. | 2nd- 132.05 | @ Westhill HS |
| Sat., 2/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | 3:10 p.m. | @ Terry Connors | |
| Sat., 2/15 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/17 | V Boys Basketball | Wilton | Away - Wilton Field House [Directions] | 7:00 p.m. | L 52-58 | |
| Mon., 2/17 | JV Boys Basketball | Wilton | Away [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Mon., 2/17 | FR Boys Basketball | Wilton | Away [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | V Boys Ice Hockey | Milford Coop | Home - Wonderland Of Ice [Directions] | 6:00 p.m. | L 0-1 | |
| Mon., 2/17 | V Boys Swimming and Diving | New Canaan | Away [Directions] | 2:00 p.m. | ||
| Mon., 2/17 | V Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | 7:00 p.m. | W 49-46 | |
| Mon., 2/17 | JV Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/17 | FR Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 7:00 p.m. | L 55-60 | |
| Wed., 2/19 | JV Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 2/19 | FR Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Boys Fencing | Guilford | Home - Fairfield Warde Small Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 8:30 p.m. | L 0-1 | Pick up and return to FLHS |
| Wed., 2/19 | V Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 42-57 | |
| Wed., 2/19 | JV Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Girls Basketball | Danbury | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Girls Fencing | Guilford | Home - Fairfield Warde Small Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/20 | V Girls Gymnastics | New Milford, Wilton | Away - New Milford High School [Directions] | 5:00 p.m. | Ludlowe- 128.8 New Milford- 122.55 | |
| Fri., 2/21 | V Wrestling | Class L States @ Bristol Central | Away | TBA | No Bus | |
| Fri., 2/21 | V Girls Gymnastics | Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 6:00 p.m. | Ludlowe- 132.05 Hand- 136.0 | |
| Sat., 2/22 | V Boys Fencing | Hopkins School | Away | 9:00 a.m. | Greenwich High school and North Haven High Schoolwill also participate in this match | |
| Sat., 2/22 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | 4:40 p.m. | L 3-8 | Pick up and return to FLHS |
| Sat., 2/22 | V Wrestling | Class L States @ Bristol Central | Away | TBA | ||
| Sat., 2/22 | V Girls Basketball | Wilton | Away [Directions] | TBA | ||
| Sat., 2/22 | V Girls Fencing | Hopkins School | Away | 9:00 a.m. | Greenwich HS and North Haven HS,will also participate in this match. | |
| Sun., 2/23 | V Boys Ice Hockey | New Canaan | Home - Wonderland Of Ice [Directions] | 7:15 p.m. | L 2-7 | |
| Mon., 2/24 | V Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 44-59 | |
| Mon., 2/24 | JV Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/24 | V Boys Fencing | North Haven | Away [Directions] | 6:00 p.m. | ||
| Mon., 2/24 | V Boys Ice Hockey | Stamford | Home - Wonderland Of Ice [Directions] | 4:50 p.m. | W 7-1 | |
| Mon., 2/24 | V Girls Fencing | North Haven | Away [Directions] | 6:00 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | FCIAC Trials at Greenwich | Away | 4:30 p.m. | ||
| Tue., 2/25 | V Bowling | Notre Dame-Fairfield | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Tue., 2/25 | V Bowling | End of year tournament | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Wed., 2/26 | V Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 7:00 p.m. | L 55-60 | |
| Wed., 2/26 | JV Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/26 | V Boys Ice Hockey | Amity | Home - Wonderland Of Ice [Directions] | 6:30 p.m. | L 3-6 | |
| Wed., 2/26 | V Boys Swimming and Diving | FCIAC Diving at Westhill | Away | 4:30 p.m. | ||
| Thu., 2/27 | V Boys Swimming and Diving | FCIAC Finals at Greenwich | Away | 6:30 p.m. | ||
| Thu., 2/27 | V Bowling | End of Year Tournament | Home - Nutmeg Lanes [Directions] | 3:00 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC Open Tourney | Away | 4:30 p.m. | @ New Haven Athletic Center | |
| Sat., 3/1 | V Boys Fencing | Individual States @ Hopkins | Away | 9:00 a.m. | ||
| Sat., 3/1 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Sat., 3/1 | V Wrestling | CIAC Open Tourney | Away | TBA | @ New Haven Athletic Center | |
| Sat., 3/1 | V Bowling | 2014 Connecticut High School Invitational Bowling Tournament | Away | 10:00 a.m. | This Tournament will be held at Silver Lanes in East Hartford | |
| Sat., 3/1 | V Girls Fencing | Individual States at Hopkins | Away | 9:00 a.m. | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Mon., 3/3 | V Girls Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 3/4 | V Boys Fencing | Daniel Hand | Away [Directions] | 5:30 p.m. | ||
| Tue., 3/4 | V Girls Fencing | Daniel Hand | Away [Directions] | 5:30 p.m. | ||
| Sat., 3/8 | V Boys Fencing | AMT Team States at Guilford High School | Away | 9:00 a.m. | ||
| Sat., 3/8 | V Girls Fencing | AMT Team States @ Guilford HS | Away | 9:00 a.m. | ||
| Thu., 3/13 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 3/13 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | ||
| Wed., 3/19 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | ||
| Wed., 3/19 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | ||
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Wed., 3/26 | V Softball | Stamford (Scrim.) | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 3/27 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Fri., 3/28 | V Baseball | Joel Barlow (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Sat., 3/29 | V Baseball | Daniel Hand (Scrim.) | Home - Kiwanis Field [Directions] | 10:00 a.m. | ||
| Sat., 3/29 | V Baseball | Immaculate (Scrim.) | Home - Kiwanis Field [Directions] | 12:30 p.m. | ||
| Sat., 3/29 | V Boys Lacrosse | Joel Barlow (Scrim.) | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 3/29 | V Girls Lacrosse | Danbury (Scrim.) | Away [Directions] | TBA | ||
| Sat., 3/29 | V Softball | Randolph HS - Randolph NJ | Home - Sturges Park [Directions] | 9:00 a.m. | ||
| Tue., 4/1 | V Baseball | Fairfield Prep (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/1 | V Co-ed Sailing | Darien (Scrim.) | Away [Directions] | 3:45 p.m. | Rules Clinic @ Darien HS | |
| Wed., 4/2 | V Baseball | Weston (Scrim.) | Home - Kiwanis Field [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | V Boys Lacrosse | Guilford (Scrim.) | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 4/2 | V Co-ed Sailing | Brunswick School | Away | 3:30 p.m. | @ TBA with Stamford and Warde | |
| Fri., 4/4 | V Softball | Brookfield (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 4/4 | JV Softball | Brookfield (Scrim.) | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Sat., 4/5 | V Baseball | Oxford (Scrim.) | Home - Kiwanis Field [Directions] | 9:30 a.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Newtown (Scrim.) | Away - Blue and Gold Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/5 | V Girls Lacrosse | Bunnell (Scrim.) | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Mon., 4/7 | V Softball | Staples (Scrim.) | Away - Wakeman Field C [Directions] | 3:45 p.m. | ||
| Mon., 4/7 | JV Softball | Staples (Scrim.) | Away - Staples HS - Softball Field [Directions] | 3:45 p.m. | JV Travels with Var | |
| Wed., 4/9 | V Baseball | Newtown | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 10-4 | |
| Wed., 4/9 | JV Baseball | Newtown | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | JV Boys Golf | Fairfield Prep, Xavier | Away [Directions] | 3:15 p.m. | ||
| Wed., 4/9 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 3-21 | |
| Wed., 4/9 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 4/9 | JV Boys Tennis | New Canaan | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Co-ed Sailing | Greenwich | Home - Pequot Yacht Club [Directions] | 3:30 p.m. | Also Brunswick School, Warde | |
| Wed., 4/9 | V Girls Golf | Darien | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | FLHS: 220 Darien: 212 | |
| Wed., 4/9 | V Girls Lacrosse | Greenwich | Home - Taft Field [Directions] | 6:00 p.m. | L 4-14 | |
| Wed., 4/9 | JV Girls Lacrosse | Greenwich | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Wed., 4/9 | V Girls Outdoor Track | Fairfield Warde, Bassick, Harding | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Softball | Stamford | Home - Sturges Park [Directions] | 4:00 p.m. | L 0-4 | |
| Wed., 4/9 | JV Softball | Stamford | Home [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Tennis | New Canaan | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/9 | JV Girls Tennis | New Canaan | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Baseball | Hamden | Away - HHS Baseball Field [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 4/10 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Trumbull: 164 Ludlowe: 178 | @ Tashua Knolls |
| Thu., 4/10 | V Boys Outdoor Track | Harding, Bassick, Fairfield Warde | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Thu., 4/10 | V Boys Tennis | Brien McMahon | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 4/10 | V Girls Golf | Wilton, Trumbull | Away - Silvermine Golf Club [Directions] | 3:15 p.m. | FLHS: 183 Wilton: 198 | @ Silvermine |
| Thu., 4/10 | JV Girls Golf | Trumbull | Home - South Pine Creek Par 3 [Directions] | 3:30 p.m. | ||
| Thu., 4/10 | V Softball | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | W 1-0 | Non-League |
| Thu., 4/10 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/10 | JV Girls Tennis | Fairfield Warde | Home - Tomlinson MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/11 | V Baseball | Harding | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 12-3 | |
| Fri., 4/11 | JV Baseball | Harding | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Boys Lacrosse | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Girls Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 7:00 p.m. | T 8-8 | |
| Fri., 4/11 | JV Girls Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Fri., 4/11 | V Softball | Harding | Away - Cal Ripken Sr. Field [Directions] | 4:00 p.m. | W 20-0 | |
| Fri., 4/11 | JV Softball | Harding | Away - Beardsley Park-Softball-JV [Directions] | 4:00 p.m. | JV Travels with Var | |
| Sat., 4/12 | V Boys Lacrosse | Mt. Greylock (MA) | Home - Taft Field [Directions] | 3:00 p.m. | W 16-4 | |
| Mon., 4/14 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | L 5-0 | |
| Mon., 4/14 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 1:00 p.m. | JV Travels with Var | |
| Mon., 4/14 | FR Baseball | Darien | Home - Kiwanis Field [Directions] | 1:00 p.m. | ||
| Mon., 4/14 | V Boys Tennis | Danbury | Home - Fairfield Ludlowe Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Mon., 4/14 | V Softball | Darien | Home - Sturges Park [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 4/14 | JV Softball | Darien | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Mon., 4/14 | V Girls Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Tue., 4/15 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 2-14 | |
| Tue., 4/15 | JV Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 4/15 | FR Boys Lacrosse | Stamford | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 4/15 | V Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 11:00 a.m. | W 13-10 | |
| Tue., 4/15 | JV Girls Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 12:30 p.m. | JV Travels with Var | |
| Wed., 4/16 | FR Baseball | Trumbull | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/16 | V Boys Tennis | Trumbull | Home - Fairfield Ludlowe Tennis Courts [Directions] | 12:30 p.m. | W 7-0 | |
| Thu., 4/17 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 2:00 p.m. | L 4-6 | |
| Thu., 4/17 | JV Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:30 p.m. | JV Travels with Var | |
| Thu., 4/17 | FR Baseball | Ridgefield | Home - Kiwanis Field [Directions] | 11:00 a.m. | ||
| Thu., 4/17 | V Boys Lacrosse | Conard | Home - Taft Field [Directions] | 12:00 p.m. | W 7-3 | |
| Thu., 4/17 | JV Boys Lacrosse | Conard | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Thu., 4/17 | FR Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 3:00 p.m. | ||
| Thu., 4/17 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 10:45 a.m. | L 8-14 | |
| Thu., 4/17 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 12:15 p.m. | JV Travels with Var | |
| Thu., 4/17 | V Softball | Ridgefield | Home - Sturges Park [Directions] | 11:00 a.m. | W 12-0(5) | |
| Thu., 4/17 | JV Softball | Ridgefield | Home - Tom Hayden field [Directions] | 11:00 a.m. | Cancelled | |
| Sat., 4/19 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 12:00 p.m. | W 6-1 | |
| Sat., 4/19 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 12:00 p.m. | JV Travels with Var | |
| Sat., 4/19 | V Boys Lacrosse | Stamford | Home - Taft Field [Directions] | 2:00 p.m. | W 10-6 | |
| Sat., 4/19 | JV Boys Lacrosse | Stamford | Home - Taft Field [Directions] | 12:00 p.m. | ||
| Sat., 4/19 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 12:00 p.m. | L 6-14 | |
| Sat., 4/19 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 10:00 a.m. | JV Travels with Var | |
| Sat., 4/19 | V Softball | Trumbull | Home - Sturges Park [Directions] | 12:00 p.m. | W 6-5(10) | |
| Sat., 4/19 | JV Softball | Trumbull | Home - Tom Hayden field [Directions] | 12:00 p.m. | ||
| Mon., 4/21 | V Baseball | Trinity Catholic | Home - Kiwanis Field [Directions] | 4:00 p.m. | L 3-6 | |
| Mon., 4/21 | JV Baseball | Trinity Catholic | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | FR Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | ||
| Mon., 4/21 | V Boys Golf | Wilton | Away - Rolling Hills [Directions] | TBA | Wilton: 173 Ludlowe: 178 | |
| Mon., 4/21 | V Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 6:30 p.m. | L 7-8 | |
| Mon., 4/21 | JV Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 4:30 p.m. | ||
| Mon., 4/21 | FR Boys Lacrosse | Norwalk | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/21 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | JV Travels with Var | |
| Mon., 4/21 | V Girls Outdoor Track | Bassick, Darien | Home - Taft Field [Directions] | 3:30 p.m. | ||
| Mon., 4/21 | V Softball | Trinity Catholic | Away - Trinity Catholic's Smith Field | 4:00 p.m. | W 11-2 | |
| Mon., 4/21 | V Girls Tennis | Staples | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/22 | V Boys Golf | Stamford | Home - Smith Richardson Golf Course [Directions] | 3:15 p.m. | Ludlowe: 163 Stamford: 201 | |
| Tue., 4/22 | JV Boys Golf | Staples | Away [Directions] | 3:15 p.m. | Cancelled | |
| Tue., 4/22 | V Boys Tennis | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/22 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | FLHS: 202 Trumbull: 207 | @ Tashua Knolls |
| Tue., 4/22 | JV Girls Golf | Darien | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 4/22 | V Girls Tennis | St. Joseph | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/23 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | 4:00 p.m. | W 12-0 | |
| Wed., 4/23 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | JV Travels with Var | |
| Wed., 4/23 | JV Boys Golf | New Canaan | Away [Directions] | 3:30 p.m. | ||
| Wed., 4/23 | FR Boys Lacrosse | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | JV Boys Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Girls Golf | Fairfield Warde, New Canaan | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | FLHS: 218 New Canaan: 253 | |
| Wed., 4/23 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:30 p.m. | ||
| Wed., 4/23 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Softball | Bridgeport Central | Home - Sturges Park [Directions] | 4:00 p.m. | W 13-0 | |
| Wed., 4/23 | JV Softball | Bridgeport Central | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Wed., 4/23 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/23 | JV Girls Tennis | Greenwich | Home - Tomlinson Middle School [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | Ludlowe:188 Danbury: 191 | |
| Thu., 4/24 | V Boys Tennis | Trinity Catholic | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/24 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | FLHS: 222 Greenwich: 184 | @ Griff Harris |
| Thu., 4/24 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:30 p.m. | ||
| Thu., 4/24 | V Girls Lacrosse | New Canaan | Home - Taft Field [Directions] | 4:00 p.m. | L 8-17 | |
| Thu., 4/24 | JV Girls Lacrosse | New Canaan | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 4/24 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | 4:00 p.m. | W 7-0 | |
| Thu., 4/24 | JV Girls Tennis | Staples | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Baseball | Bassick | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 30-5 | |
| Fri., 4/25 | FR Boys Lacrosse | Brien McMahon | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Co-ed Sailing | Staples | Home - Pequot Yacht Club [Directions] | 3:30 p.m. | also Warde and Darien | |
| Fri., 4/25 | FR Girls Lacrosse | Greenwich | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 4/25 | V Softball | Bassick | Away - Went Field [Directions] | 4:00 p.m. | W 18-0 | |
| Sat., 4/26 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | L 7-8 | |
| Sat., 4/26 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 2:00 p.m. | ||
| Sat., 4/26 | V Co-ed Sailing | States at Coast Guard Academy | Away | 9:00 a.m. | ||
| Mon., 4/28 | V Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | Staples: 156 Ludlowe: 171 | |
| Mon., 4/28 | V Boys Outdoor Track | Brien McMahon, St. Joseph | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Boys Tennis | Wilton | Away - WHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 4/28 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | JV Travels with Var | |
| Mon., 4/28 | V Co-ed Sailing | Stamford | Home - Pequot Yacht Club [Directions] | 3:30 p.m. | also Prep, Warde | |
| Mon., 4/28 | JV Girls Golf | Staples | Away - Longshore [Directions] | TBA | ||
| Mon., 4/28 | V Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | 3:45 p.m. | W 17-5 | |
| Mon., 4/28 | JV Girls Lacrosse | Norwalk | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 4/28 | V Girls Outdoor Track | St. Joseph, Brien McMahon | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Girls Tennis | Wilton | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 4/28 | JV Girls Tennis | Wilton | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | JV Boys Golf | Staples | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/29 | V Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 7:00 p.m. | L 4-5 | |
| Tue., 4/29 | JV Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 4/29 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 3:45 p.m. | JV Travels with Var | |
| Tue., 4/29 | V Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | FLHS:218 Staples: 188 | @ Longshore |
| Tue., 4/29 | JV Girls Golf | Trumbull | Away - The Glen at Tashua Knolls [Directions] | 3:15 p.m. | ||
| Tue., 4/29 | FR Girls Lacrosse | Trumbull | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Tue., 4/29 | V Softball | Staples | Home - Sturges Park [Directions] | 4:00 p.m. | W 14-0(5) | |
| Tue., 4/29 | JV Softball | Staples | Home - Tom Hayden field [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 4/29 | V Girls Tennis | Fairfield Warde | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/29 | JV Girls Tennis | Fairfield Warde | Home - Tomlinson MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/30 | JV Boys Golf | Amity | Away [Directions] | 3:00 p.m. | Cancelled | @ Woodbridge CC |
| Wed., 4/30 | JV Boys Golf | Darien | Away [Directions] | 3:30 p.m. | Cancelled | @ Woodway CC |
| Wed., 4/30 | JV Boys Golf | Darien, Fairfield Warde, New Canaan | Away [Directions] | 3:30 p.m. | @ Wee Burn CC | |
| Wed., 4/30 | V Co-ed Sailing | Greens Farms Academy | Away | @ Peqout with Greenwich Academy and Warde | ||
| Thu., 5/1 | JV Boys Golf | Darien | Away [Directions] | 3:30 p.m. | Cancelled | @ Woodway CC |
| Thu., 5/1 | JV Girls Golf | Greenwich | Away [Directions] | 3:30 p.m. | Cancelled | Course TBA |
| Thu., 5/1 | V Girls Lacrosse | Cheshire | Home - Taft Field [Directions] | 4:30 p.m. | L 14-19 | |
| Thu., 5/1 | JV Girls Lacrosse | Cheshire | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 5/1 | JV Girls Tennis | Harding | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Baseball | Brien McMahon | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 5/2 | JV Baseball | Brien McMahon | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Boys Lacrosse | Jonathan Law | Home - Taft Field [Directions] | 5:00 p.m. | W 15-1 | |
| Fri., 5/2 | FR Boys Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Fri., 5/2 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Fri., 5/2 | FR Girls Lacrosse | Ridgefield | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 15-1 | |
| Fri., 5/2 | JV Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | JV Travels with Var | |
| Fri., 5/2 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Sat., 5/3 | V Baseball | Staples | Away - Staples Baseball Field [Directions] | 3:00 p.m. | L 2-10 | |
| Sat., 5/3 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 3:00 p.m. | JV Travels with Var | |
| Sat., 5/3 | FR Baseball | Brien McMahon | Away - Roton [Directions] | 11:00 a.m. | ||
| Sat., 5/3 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 3:00 p.m. | W 12-4 | |
| Sat., 5/3 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Sat., 5/3 | FR Boys Lacrosse | East Lyme | Home - Taft Field [Directions] | 9:00 a.m. | ||
| Sat., 5/3 | V Girls Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | 3:00 p.m. | W 19-5 | |
| Sat., 5/3 | JV Girls Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | 4:30 p.m. | JV Travels with Var | |
| Sat., 5/3 | V Girls Tennis | Newtown | Away - Newtown High School [Directions] | 3:00 p.m. | W 6-1 | |
| Mon., 5/5 | V Baseball | Norwalk | Away - City Hall Field [Directions] | 4:30 p.m. | L 6-4 | |
| Mon., 5/5 | JV Baseball | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:30 p.m. | JV Travels with Var | |
| Mon., 5/5 | FR Baseball | Norwalk | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Boys Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | New Canaan: 165 Ludlowe: 169 | |
| Mon., 5/5 | V Boys Tennis | Stamford | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/5 | V Girls Outdoor Track | Ridgefield, Westhill | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Mon., 5/5 | V Softball | Norwalk | Home - Sturges Park [Directions] | 4:30 p.m. | W 8-4 | |
| Mon., 5/5 | JV Softball | Norwalk | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Mon., 5/5 | V Girls Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/6 | FR Baseball | Staples | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Golf | Trinity Catholic | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Ludlowe: 173 Trinity Catholic: 177 | |
| Tue., 5/6 | JV Boys Golf | Amity, Fairfield Warde | Away [Directions] | 3:30 p.m. | @ Woodbridge CC | |
| Tue., 5/6 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 7:00 p.m. | L 5-12 | |
| Tue., 5/6 | JV Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/6 | V Boys Outdoor Track | Ridgefield, Westhill | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 5/6 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | JV Travels with Var | |
| Tue., 5/6 | V Girls Golf | Darien | Away - CC of Darien [Directions] | 3:00 p.m. | FLHS: 230 Darien: 224 | @ CC of Darien |
| Tue., 5/6 | JV Girls Golf | Greenwich | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/6 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 18-3 | |
| Tue., 5/6 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | JV Travels with Var | |
| Tue., 5/6 | V Girls Tennis | Ridgefield | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/6 | JV Girls Tennis | Ridgefield | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Baseball | Greenwich | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/7 | JV Baseball | Greenwich | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Boys Golf | Brien McMahon | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Ludlowe: 163 Brien McMahon: 185 | |
| Wed., 5/7 | V Co-ed Sailing | Darien | Away [Directions] | 3:30 p.m. | @ TBA with Warde and Stamford | |
| Wed., 5/7 | V Girls Golf | Danbury | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | FLHS: 228 Danbury: 193 | |
| Wed., 5/7 | JV Girls Golf | Trumbull | Home - South Pine Creek Par 3 [Directions] | 3:30 p.m. | ||
| Wed., 5/7 | FR Girls Lacrosse | Staples | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 4:00 p.m. | L 5-8 | |
| Wed., 5/7 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | JV Travels with Var | |
| Wed., 5/7 | JV Girls Tennis | Darien | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | JV Baseball | Stamford | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/9 | FR Baseball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | V Co-ed Sailing | Fairfield Prep | Away - Pequot Yacht Club [Directions] | 3:30 p.m. | with Warde and GFA | |
| Fri., 5/9 | FR Girls Lacrosse | Wilton | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/9 | JV Softball | Stamford | Away - Cummings Park [Directions] | 4:00 p.m. | JV Travels with Var | |
| Sat., 5/10 | V Baseball | Stamford | Home - Kiwanis Field [Directions] | 9:30 a.m. | W 6-5 | |
| Sat., 5/10 | V Boys Lacrosse | Staples | Home - Taft Field [Directions] | 2:00 p.m. | L 4-9 | |
| Sat., 5/10 | JV Boys Lacrosse | Staples | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 12:00 p.m. | L 9-12 | |
| Sat., 5/10 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 10:30 a.m. | JV Travels with Var | |
| Sat., 5/10 | V Softball | Stamford | Away - Stamford High School [Directions] | 12:00 p.m.. | W 6-5 | |
| Sun., 5/11 | V Co-ed Sailing | Fairfield Cup | Home - Pequot Yacht Club [Directions] | 12:00 p.m. | ||
| Mon., 5/12 | V Baseball | Fairfield Warde | Away - Harbor Yard Stadium [Directions] | 6:00 p.m. | L 5-7 | |
| Mon., 5/12 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 3:45 p.m. | No Return - Car Pool to Harbor Yard | |
| Mon., 5/12 | FR Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | 3:45 p.m. | ||
| Mon., 5/12 | V Boys Golf | Westhill | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Ludlowe: 162 Westhill: 171 | |
| Mon., 5/12 | V Boys Lacrosse | St. Joseph | Home - Taft Field [Directions] | 7:30 p.m. | W 8-6 | |
| Mon., 5/12 | JV Boys Lacrosse | St. Joseph | Home - Sturges Park [Directions] | 5:30 p.m. | ||
| Mon., 5/12 | V Boys Tennis | Greenwich | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 5/12 | JV Boys Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Girls Outdoor Track | Norwalk, Stamford | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Softball | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | W 2-1(9) | |
| Mon., 5/12 | JV Softball | Fairfield Warde | Home - Tom Hayden field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Mon., 5/12 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | JV Travels with Var | |
| Tue., 5/13 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:00 p.m. | Ludlowe: 160 Ridgefield: 145 | |
| Tue., 5/13 | JV Boys Golf | Wilton | Away [Directions] | 3:30 p.m. | @ Rolling Hills CC | |
| Tue., 5/13 | JV Boys Golf | Fairfield Prep | Away [Directions] | 3:30 p.m. | @ Brooklawn | |
| Tue., 5/13 | V Boys Outdoor Track | Norwalk, Stamford | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Tue., 5/13 | V Boys Tennis | Bridgeport Central | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/13 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 3:45 p.m. | Shuttle Bus - No Return | |
| Tue., 5/13 | V Girls Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | FLHS: 214 Wilton: 240 | |
| Tue., 5/13 | JV Girls Golf | Staples | Away [Directions] | 3:30 p.m. | @ Longshore | |
| Tue., 5/13 | V Girls Lacrosse | Ridgefield | Home - Taft Field [Directions] | 7:00 p.m. | W 15-14 | |
| Tue., 5/13 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 5/14 | V Baseball | Westhill | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 5/14 | JV Baseball | Westhill | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | JV Boys Golf | Darien, Fairfield Warde, New Canaan | Away - Woodway CC [Directions] | 3:15 p.m. | Cancelled | @ Woodway CC |
| Wed., 5/14 | V Boys Lacrosse | Wilton | Home - Taft Field [Directions] | 7:00 p.m. | L 9-10 OT | |
| Wed., 5/14 | JV Boys Lacrosse | Wilton | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 5/14 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Tennis | Norwalk | Away - Norwalk High Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/14 | JV Girls Golf | Darien | Away - CC of Darien [Directions] | 3:00 p.m. | ||
| Wed., 5/14 | FR Girls Lacrosse | Trumbull | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 5/14 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | 4:15 p.m. | L 5-6 | |
| Wed., 5/14 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | JV Travels with Var | |
| Wed., 5/14 | V Girls Tennis | Norwalk | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/14 | JV Girls Tennis | Harding | Home - Tomlinson Middle School [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 4-2 | |
| Thu., 5/15 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:15 p.m. | JV Travels with Var | |
| Thu., 5/15 | FR Baseball | Wilton | Home - Kiwanis Field [Directions] | 4:30 p.m. | ||
| Thu., 5/15 | FR Boys Lacrosse | Darien | Home - Sturges Park [Directions] | 4:30 p.m. | ||
| Thu., 5/15 | V Boys Tennis | Westhill | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 5/15 | V Girls Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:00 p.m. | FLHS: 211 FWHS: 188 | |
| Thu., 5/15 | V Softball | Wilton | Home - Sturges Park [Directions] | 4:30 p.m. | W 14-4 | |
| Thu., 5/15 | V Girls Tennis | Westhill | Home - Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 5/16 | FR Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 5/16 | FR Girls Lacrosse | Fairfield Warde | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 5/17 | V Boys Lacrosse | Wellesley (MA) | Away | 3:00 p.m. | L 5-10 | |
| Sat., 5/17 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 22-7 | |
| Sat., 5/17 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | JV Travels with Var | |
| Mon., 5/19 | V Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/19 | JV Baseball | Danbury | Away - Danbury High School Junior Varsity Baseball Field [Directions] | 4:00 p.m. | JV Travels with Var | |
| Mon., 5/19 | FR Baseball | Danbury | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Boys Golf | St. Joseph, Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:15 p.m. | Fairfield Warde: 161 Fairfield Ludlowe: 170 St. Joseph: 195 | |
| Mon., 5/19 | V Boys Lacrosse | Trinity Catholic | Home - Taft Field [Directions] | 6:00 p.m. | W 13-1 | |
| Mon., 5/19 | JV Boys Lacrosse | Bridgeport Central | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | FR Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/19 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/19 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 5/19 | V Girls Outdoor Track | Greenwich, New Canaan | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Softball | Danbury | Home - Sturges Park [Directions] | 3:30 p.m. | L 2-4 | |
| Mon., 5/19 | JV Softball | Danbury | Home - Tom Hayden field [Directions] | 3:30 p.m. | ||
| Mon., 5/19 | V Girls Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 5/19 | JV Girls Tennis | Darien | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | JV Boys Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | Greenwich, New Canaan | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 5-18 | |
| Tue., 5/20 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | JV Travels with Var | |
| Wed., 5/21 | V Baseball | St. Joseph | Home - Kiwanis Field [Directions] | 4:00 p.m. | L 4-3 | |
| Wed., 5/21 | JV Baseball | St. Joseph | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | FR Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Boys Golf | Bassick, Bridgeport Central, Harding | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Fairfield Ludlowe: 161 Bridgeport Central: 251 Harding: 248 | |
| Wed., 5/21 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | FLHS:210 FWHS: 198 | @ Smith Richardson |
| Wed., 5/21 | V Girls Lacrosse | St. Joseph | Home - Taft Field [Directions] | 6:30 p.m. | W 20-7 | |
| Wed., 5/21 | JV Girls Lacrosse | St. Joseph | Home - Taft Field [Directions] | 4:45 p.m. | ||
| Wed., 5/21 | V Softball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | L 1-7 | |
| Wed., 5/21 | JV Softball | St. Joseph | Away - Unity Park, Trumbull [Directions] | 4:00 p.m. | JV Travels with Var | |
| Wed., 5/21 | V Girls Tennis | Ridgefield | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | FCIAC Quarterfinals |
| Thu., 5/22 | V Boys Outdoor Track | Darien, Bassick | Away - DHS Track [Directions] | 4:00 p.m. | ||
| Thu., 5/22 | FR Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/23 | V Baseball | New Canaan | Home - Kiwanis Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 5/23 | JV Baseball | New Canaan | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Girls Lacrosse | Darien | Away [Directions] | 4:00 p.m. | L 3-11 | FCIAC Quarterfinals |
| Fri., 5/23 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | Cancelled | JV Travels with Var |
| Fri., 5/23 | V Girls Tennis | Staples | Home - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 4-2 | FCIAC Semi-Finals |
| Sat., 5/24 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 1:30 p.m. | W 6-4(9) | |
| Tue., 5/27 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:15 p.m. | FCIAC Quarterfinals | |
| Tue., 5/27 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | Greenwich: 149 Fairfield Ludlowe: 174 | |
| Tue., 5/27 | JV Boys Golf | Darien, Fairfield Warde | Home [Directions] | 3:30 p.m. | ||
| Tue., 5/27 | V Boys Outdoor Track | FCIAC Championship | Away | 2:00 p.m. | @ Danbury HS | |
| Tue., 5/27 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | FLHS: 226 New Canaan 235 | @ CC of New Canaan |
| Tue., 5/27 | V Girls Outdoor Track | FCIAC Championships | Away | 2:00 p.m. | @ Danbury HS | |
| Tue., 5/27 | V Softball | Stamford | Home - Sturges Park [Directions] | 4:00 p.m. | L 5-6 | FCIAC Quarterfinals |
| Wed., 5/28 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Fairfield Ludlowe: 175 Norwalk: 179 | |
| Wed., 5/28 | V Girls Golf | Ridgefield | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | FLHS:202 Ridgefield: 190 | |
| Wed., 5/28 | V Girls Golf | Darien, New Canaan, Danbury | Away [Directions] | TBA | Cancelled | @ Fairfield Wheeler |
| Wed., 5/28 | JV Girls Golf | JV Tourney at SPC | Home - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Wed., 5/28 | V Girls Tennis | Greenwich | Away [Directions] | 4:00 p.m. | W 4-3 | FCIAC Championship |
| Thu., 5/29 | V Boys Golf | Darien | Away - Woodway CC [Directions] | 3:15 p.m. | Cancelled | |
| Sat., 5/31 | V Boys Lacrosse | Shelton | Away [Directions] | 1:00 p.m. | W 16-10 | CIAC States Playdown |
| Sun., 6/1 | V Girls Lacrosse | Norwich Free Academy | Away - NFA Turf Field [Directions] | 2:30 p.m. | W 22-4 | CIAC Playdown |
| Mon., 6/2 | V Baseball | New Britain | Home - Kiwanis Field [Directions] | 4:00 p.m. | L 5-4 | CIAC LL First Round |
| Mon., 6/2 | V Softball | New Milford | Home - Sturges Park [Directions] | 4:00 p.m. | W 13-6 | CIAC LL First Round |
| Mon., 6/2 | V Girls Tennis | Conard | Home - Fairfield Ludlowe Tennis Courts [Directions] | 3:00 p.m. | CIAC First Round | |
| Tue., 6/3 | V Girls Lacrosse | Simsbury | Away - Simsbury High School [Directions] | 5:00 p.m. | L 14-20 | CIAC First Round |
| Tue., 6/3 | V Softball | Cheshire | Away - Cheshire High softball field [Directions] | 4:00 p.m. | L 1-3 | CIAC LL Second Round |
| Tue., 6/3 | V Girls Tennis | South Windsor | Home - Fairfield Ludlowe Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | CIAC Quarterfinals |
| Wed., 6/4 | V Boys Lacrosse | Greenwich | Away [Directions] | 5:00 p.m. | CIAC States First Round | |
| Wed., 6/4 | V Girls Golf | FCIAC's | Away | 9:00 a.m. | @ Fairchild Wheeler | |
| Wed., 6/4 | V Girls Tennis | Amity | Home - Fairfield Ludlowe Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | CIAC Semi-Finals |
| Fri., 6/6 | V Girls Tennis | Darien | Away - Wilton HS Tennis Courts [Directions] | 3:00 p.m. | CIAC Class L Championship | |
| Tue., 6/10 | V Girls Golf | CIAC Tourney | Away | 8:00 a.m. | @ Orange Hills | |