| Fairfield Ludlowe 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 878 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | TBA | JV Travels with Varsity | |
| TBA | FR Baseball | St. Joseph | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| TBA | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | TBA | PU:2:30 RE:5;30 | |
| TBA | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | TBA | PU:2:30 RE:5;30 | |
| TBA | JV Boys Tennis | New Canaan | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Tennis | Darien | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| TBA | V Co-ed Alpine Skiing | State Championship | Away | 3:00 p.m. | PU FLHS 11:55, FWHS 12:10, RE 6pm | |
| TBA | V Co-ed Alpine Skiing | State Tournament | Away | TBA | TBA | |
| TBA | V Bowling | Playoffs | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| TBA | JV Bowling | Playoffs | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| TBA | JV Girls Golf | Darien | Home [Directions] | 3:30 p.m. | ||
| TBA | V Softball | Kennedy (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Brookfield | Away - PTAK Softball Field [Directions] | Cancelled | JV Travels with Varsity | |
| Sat., 8/23 | V Football | Foran (Scrim.) | Away [Directions] | 11:00 a.m. | PU:9:00am RE:12:30 | 2 Buses |
| Tue., 8/26 | V Football | Jonathan Law (Scrim.) | Away - Jonathan Law HS Stadium [Directions] | 3:30 p.m. | ||
| Thu., 8/28 | V Boys Soccer | New Milford (Scrim.) | Home - Taft Field [Directions] | 6:30 p.m. | ||
| Sat., 8/30 | V Field Hockey | Norwalk (Scrim.) | Away [Directions] | TBA | PU:TBA | |
| Sat., 8/30 | V Girls Soccer | Shelton (Scrim.) | Away [Directions] | TBA | PU:TBA | |
| Tue., 9/2 | V Field Hockey | Bethel (Scrim.) | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Tue., 9/2 | JV Field Hockey | Bethel (Scrim.) | Home - Taft Field [Directions] | 5:15 p.m. | ||
| Tue., 9/2 | V Girls Volleyball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 3:45 p.m. | PU:2:30 RE:5:30 | |
| Wed., 9/3 | V Boys Soccer | Weston (Scrim.) | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 9/3 | V Girls Soccer | Bethel (Scrim.) | Away - Bethel High School [Directions] | 3:45 p.m. | 2:30 RE:5:15 | |
| Fri., 9/5 | V Football | Platt Tech (Scrim.) | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Fri., 9/5 | V Field Hockey | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 4:30 p.m. | PU:3:15 RE:6:00 | |
| Fri., 9/5 | V Girls Soccer | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 5:00 p.m. | PU:3:30 RE:6:30 | |
| Sat., 9/6 | V Boys Soccer | Newtown (Scrim.) | Away - Newtown High School Practice Field [Directions] | 9:00 a.m. | PU:7:30am RE:10:30 | |
| Sat., 9/6 | V Girls Volleyball | Staples (Scrim.) | Away [Directions] | 9:00 a.m. | PUDO:8:00 REPU:TBA | |
| Tue., 9/9 | V Boys Cross Country | Danbury, Greenwich, Norwalk | Away - Tarrywile Park [Directions] | 4:00 p.m. | PU:2:20 RE:6:00 | |
| Tue., 9/9 | V Boys Soccer | Darien | Home - Taft Field [Directions] | W 3-0 | ||
| Tue., 9/9 | JV Boys Soccer | Darien | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Tue., 9/9 | FR Boys Soccer | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 9/9 | V Girls Cross Country | Danbury, Greenwich, Norwalk | Away - Tarrywile Park [Directions] | 4:00 p.m. | PU:2:20 RE:6:00 | |
| Tue., 9/9 | FR Field Hockey | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | PU:2:30 RE:5:00 | |
| Wed., 9/10 | V Field Hockey | Greenwich | Home - Taft Field [Directions] | T 1-1 | ||
| Wed., 9/10 | JV Field Hockey | Greenwich | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Wed., 9/10 | V Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | L 0-1 | PU:2:15 RE:6:30 | |
| Wed., 9/10 | JV Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Wed., 9/10 | FR Girls Soccer | Danbury | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Wed., 9/10 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Wed., 9/10 | V Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Wed., 9/10 | JV Girls Volleyball | Staples | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 9/10 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Thu., 9/11 | FR Football | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | 4:30 p.m. | PU:2:30 RE:6:00 | |
| Thu., 9/11 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 2-0 | PU:2:30 RE:5:30 | |
| Thu., 9/11 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 9/11 | FR Boys Soccer | Stamford | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Fri., 9/12 | V Football | Lyman Hall | Home - Taft Field [Directions] | W 43-0 | ||
| Fri., 9/12 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | W 2-1 | PU:3:00 RE:6:00 | Non-League |
| Fri., 9/12 | JV Field Hockey | St. Joseph | Away - St. Joseph High School [Directions] | 3:30 p.m. | PU:2:20 RE:4:45 | |
| Fri., 9/12 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 5-0 | PU:2:45 RE:5:15 | |
| Fri., 9/12 | JV Girls Soccer | Bassick | Away [Directions] | 4:00 p.m. | PU:3:00 RE:5:15 | |
| Fri., 9/12 | FR Girls Soccer | Fairfield Warde | Home - South Pine Creek Field [Directions] | Cancelled | ||
| Fri., 9/12 | V Girls Swimming and Diving | St. Joseph | Away - Hillcrest MS, Trumbull, CT [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Fri., 9/12 | V Girls Volleyball | Danbury | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/12 | JV Girls Volleyball | Danbury | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 9/12 | FR Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:30 p.m. | PU:3:00 RE:5:45 | |
| Sat., 9/13 | JV Football | Lyman Hall | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Mon., 9/15 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | L 0-2 | PU:2:30 RE:6:30 | |
| Mon., 9/15 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Mon., 9/15 | FR Field Hockey | New Canaan | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Mon., 9/15 | V Girls Soccer | Trumbull | Home - Taft Field [Directions] | T 0-0 | ||
| Mon., 9/15 | JV Girls Soccer | Trumbull | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 9/15 | FR Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Mon., 9/15 | V Girls Volleyball | Bridgeport Central | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Mon., 9/15 | JV Girls Volleyball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Tue., 9/16 | V Boys Cross Country | Wilton, Westhill, Bassick, Darien | Away - Allen's Meadow [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | |
| Tue., 9/16 | V Boys Soccer | St. Joseph | Home - Taft Field [Directions] | W 4-0 | ||
| Tue., 9/16 | JV Boys Soccer | St. Joseph | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Tue., 9/16 | FR Boys Soccer | Fairfield Warde | Home - Roger Ludlowe Middle School [Directions] | 3:45 p.m. | ||
| Tue., 9/16 | V Girls Cross Country | Wilton, Westhill, Bassick, Darien | Away - Allen's Meadow [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | |
| Wed., 9/17 | V Girls Soccer | Wilton | Home - Taft Field [Directions] | T 2-2 | ||
| Wed., 9/17 | JV Girls Soccer | Wilton | Home - Sturges Park [Directions] | 4:30 p.m. | ||
| Wed., 9/17 | FR Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Wed., 9/17 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-0 | PU:2:30 RE:6:30 | |
| Wed., 9/17 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 9/18 | FR Football | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | PU:2:30 RE:6:00 | |
| Thu., 9/18 | V Boys Soccer | Westhill | Home - Taft Field [Directions] | W 2-0 | ||
| Thu., 9/18 | JV Boys Soccer | Westhill | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Fri., 9/19 | V Football | Ridgefield | Home - Taft Field [Directions] | W 13-10 | ||
| Fri., 9/19 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | L 0-6 | PU:2:30 RE:6:30 | |
| Fri., 9/19 | JV Field Hockey | Wilton | Away - Wilton High School - Grass Field [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Fri., 9/19 | FR Field Hockey | Wilton | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Girls Soccer | St. Joseph | Away - St. Joseph High School [Directions] | L 0-2 | PU:2:30 RE:5:30 | |
| Fri., 9/19 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 9/19 | FR Girls Soccer | Trumbull | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Girls Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | W 3-0 | PU:3:00 RE:6:30 | |
| Fri., 9/19 | JV Girls Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Sat., 9/20 | JV Football | Ridgefield | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 9/20 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 1:00 p.m. | PU:11:00 RE:2:00 | |
| Sat., 9/20 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | L 1-3 | PU:9:15 RE:1:00 | Non-League |
| Sat., 9/20 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 10:30 a.m. | JV Travels with Varsity | |
| Mon., 9/22 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | W 2-0 | PU:2:30 RE:5:30 | |
| Mon., 9/22 | V Field Hockey | Brien McMahon | Home - Taft Field [Directions] | W 1-0 | ||
| Mon., 9/22 | JV Field Hockey | Brien McMahon | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Mon., 9/22 | V Girls Volleyball | Wilton | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Mon., 9/22 | JV Girls Volleyball | Wilton | Home - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 9/22 | FR Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | 4:30 p.m. | PU:3:00 RE:5:45 | |
| Tue., 9/23 | V Boys Cross Country | St. Joseph, Bassick, Stamford, Brien McMahon | Away - St. Joseph High School [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | |
| Tue., 9/23 | V Boys Soccer | Fairfield Warde | Home - Taft Field [Directions] | W 3-1 | ||
| Tue., 9/23 | JV Boys Soccer | Fairfield Warde | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Tue., 9/23 | V Girls Cross Country | St. Joseph, Bassick, Stamford, Brien McMahon | Away [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | |
| Tue., 9/23 | V Girls Soccer | Staples | Home - Taft Field [Directions] | L 2-6 | ||
| Tue., 9/23 | JV Girls Soccer | Staples | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Tue., 9/23 | V Girls Swimming and Diving | Ridgefield | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/23 | V Girls Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Tue., 9/23 | JV Girls Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Tue., 9/23 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:15 p.m. | PU:3:00 RE:5:30 | |
| Fri., 9/26 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | L 21-24 | PU:4:30 RE:8:30 | 2 Buses |
| Fri., 9/26 | FR Football | Bridgeport Central | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Fri., 9/26 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | PU:3:00 | |
| Fri., 9/26 | V Competitive Cheerleading | Bridgeport Central | Away [Directions] | 7:00 p.m. | PU:5:45 RE:8:30 | |
| Fri., 9/26 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-3 | PU:1:45 RE:5:15 | JV Travels with Varsity |
| Fri., 9/26 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 3:45 p.m. | JV Travels with Varsity | |
| Fri., 9/26 | FR Girls Soccer | Ridgefield | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Sat., 9/27 | V Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | T 2-2 | PUDOJV:11:45 PUDOV:1:30 RE:4:30 | |
| Sat., 9/27 | JV Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 3:00 p.m. | JV Shuttles with Varsith | |
| Sat., 9/27 | FR Boys Soccer | Trumbull | Home - Sturges Park [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | V Field Hockey | Westhill | Home - Taft Field [Directions] | L 0-2 | ||
| Sat., 9/27 | JV Field Hockey | Westhill | Home - Taft Field [Directions] | 9:30 a.m. | ||
| Sat., 9/27 | FR Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | Cancelled | PU:9:30 RE:12:30 | |
| Mon., 9/29 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 9/29 | V Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | L 0-2 | PU:2:20 RE:6:30 | |
| Mon., 9/29 | JV Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Mon., 9/29 | FR Field Hockey | Danbury | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Mon., 9/29 | V Girls Soccer | Norwalk | Home - Taft Field [Directions] | W 7-0 | ||
| Mon., 9/29 | FR Girls Soccer | Greenwich | Home - South Pine Creek Field [Directions] | 4:00 p.m. | ||
| Mon., 9/29 | V Girls Swimming and Diving | Danbury | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/29 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | PU:2:30 RE:6:30 | |
| Mon., 9/29 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Mon., 9/29 | FR Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Boys Cross Country | Staples, Ridgefield, Bassick, Trumbull, Bridgeport Central | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | T 1-1 | PU:2:20 RE:5:30 | |
| Tue., 9/30 | JV Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Tue., 9/30 | FR Boys Soccer | Danbury | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Tue., 9/30 | V Girls Cross Country | Staples, Ridgefield, Bassick, Trumbull, Bridgeport Central | Home [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | L 0-4 | PU:4:00 RE:8:30 | |
| Wed., 10/1 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Wed., 10/1 | FR Field Hockey | Trumbull | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Girls Soccer | Stamford | Home - Taft Field [Directions] | W 5-0 | ||
| Wed., 10/1 | JV Girls Soccer | Stamford | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Girls Swimming and Diving | New Canaan | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/1 | V Girls Volleyball | Trinity Catholic | Away | W 3-1 | PU:2:30 RE:6:30 | |
| Wed., 10/1 | JV Girls Volleyball | Trinity Catholic | Away | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 10/2 | V Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | W 47-40 | PU:1:30 RE:5:30 | 2 Buses |
| Thu., 10/2 | FR Football | Harding | Home - Taft Field [Directions] | Cancelled | ||
| Thu., 10/2 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | T 1-1 | PU:5:30 RE:8:45 | |
| Thu., 10/2 | JV Boys Soccer | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Thu., 10/2 | FR Boys Soccer | Norwalk | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Thu., 10/2 | V Competitive Cheerleading | Harding | Away [Directions] | 3:30 p.m. | PU:2:15 RE:5:00 | |
| Mon., 10/6 | JV Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/6 | V Boys Soccer | Brien McMahon | Home - Taft Field [Directions] | W 2-0 | ||
| Mon., 10/6 | JV Boys Soccer | Brien McMahon | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Mon., 10/6 | V Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | L 2-3 | PU:2:30 RE:5:30 | |
| Mon., 10/6 | JV Girls Soccer | Greenwich | Home - Sturges Park [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Mon., 10/6 | V Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 3-0 | PU:2:45 RE:6:30 | |
| Mon., 10/6 | JV Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Tue., 10/7 | V Boys Cross Country | Fairfield Warde, Bassick, Harding, New Canaan, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | FR Boys Soccer | Fairfield Country Day School | Away | 3:45 p.m. | PUDO:2:30 No Return | |
| Tue., 10/7 | V Girls Cross Country | Fairfield Warde, Bassick, Harding, New Canaan, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | V Field Hockey | Darien | Home - Taft Field [Directions] | L 1-3 | ||
| Tue., 10/7 | JV Field Hockey | Darien | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 10/7 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:15 | |
| Wed., 10/8 | V Boys Soccer | Bridgeport Central | Home - Taft Field [Directions] | W 7-2 | ||
| Wed., 10/8 | JV Boys Soccer | Bridgeport Central | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University- Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/8 | V Girls Volleyball | Stamford | Away - Stamford High School [Directions] | L 2-3 | PU:2:30 RE:6:30 | |
| Wed., 10/8 | JV Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Wed., 10/8 | FR Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/9 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | PU:2:45 RE:5:30 | |
| Thu., 10/9 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 1-0(OT) | PU:2:30 RE:6:15 | |
| Thu., 10/9 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 3:30 p.m. | JV Travels with Varsity | |
| Thu., 10/9 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 1-0 | PUDO:5:00 RE:8:30 | |
| Thu., 10/9 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | PUDO:2:45 No Return | |
| Thu., 10/9 | FR Girls Soccer | Fairfield Warde | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 10/10 | V Football | Staples | Home - Taft Field [Directions] | L 7-34 | ||
| Fri., 10/10 | V Boys Soccer | Staples | Home - Taft Field [Directions] | W 2-1 | ||
| Fri., 10/10 | JV Boys Soccer | Staples | Home - Sturges Park [Directions] | 3:45 p.m. | ||
| Fri., 10/10 | FR Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Fri., 10/10 | FR Field Hockey | Staples | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Fri., 10/10 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | PU:1:45 RE:4:30 | |
| Fri., 10/10 | V Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/10 | JV Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 10/10 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Sat., 10/11 | V Field Hockey | Weston | Away - WHS Turf Field [Directions] | W 2-1 | PU:8:30 RE:12:30 | Non-League |
| Mon., 10/13 | JV Football | Staples | Home - Taft Field [Directions] | 6:30 p.m. | ||
| Mon., 10/13 | V Boys Soccer | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | W 7-0 | PU:2:45 RE:5:30 | |
| Mon., 10/13 | V Girls Soccer | Darien | Home - Taft Field [Directions] | L 1-3 | ||
| Mon., 10/13 | JV Girls Soccer | Darien | Home - Sturges Park [Directions] | 4:15 p.m. | ||
| Tue., 10/14 | V Field Hockey | Ridgefield | Home - Taft Field [Directions] | L 0-1 | ||
| Tue., 10/14 | JV Field Hockey | Ridgefield | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 10/14 | FR Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Tue., 10/14 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 3-0 | PU:2:30 RE:6:30 | |
| Tue., 10/14 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Tue., 10/14 | FR Girls Volleyball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/15 | FR Football | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | PU:4:45 RE:8:30 | 2 Buses |
| Wed., 10/15 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:15 | |
| Wed., 10/15 | V Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 3-0 | PU:2:45 RE:6:30 | |
| Wed., 10/15 | JV Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Thu., 10/16 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 0-3 | PU:4:30 RE:8:30 | |
| Thu., 10/16 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | JV Travels with Varsity | |
| Thu., 10/16 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | L 0-3 | PU:2:30 RE:5:30 | |
| Thu., 10/16 | JV Girls Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 10/17 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 3-1 | PU:2:00 RE:5:15 | |
| Fri., 10/17 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 3:45 p.m. | JV Travels with Varsity | |
| Fri., 10/17 | FR Boys Soccer | Ridgefield | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Fri., 10/17 | FR Field Hockey | Norwalk | Home - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Fri., 10/17 | V Girls Soccer | Trinity Catholic | Home - Taft Field [Directions] | W 7-0 | ||
| Fri., 10/17 | JV Girls Soccer | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | PU:3:00 RE:5:30 | |
| Fri., 10/17 | V Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/17 | JV Girls Volleyball | New Canaan | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 10/17 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:30 p.m. | PU:3:00 RE:5:30 | |
| Sat., 10/18 | V Football | Norwalk | Home - Taft Field [Directions] | L 14-16 | ||
| Sat., 10/18 | JV Field Hockey | Weston | Away - WHS Turf Field [Directions] | Cancelled | JV Travels with Varsity | |
| Mon., 10/20 | V Boys Cross Country | FCIAC Championship | Away | 3:20 p.m. | PUDO:12:30 REPU:5:00 | |
| Mon., 10/20 | JV Football | Norwalk | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Mon., 10/20 | V Boys Soccer | New Canaan | Home - Taft Field [Directions] | W 3-1 | ||
| Mon., 10/20 | JV Boys Soccer | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/20 | FR Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 10/20 | V Girls Cross Country | FCIAC Championship | Away | 3:30 p.m. | PUDO:12:30 REPU:5:00 | |
| Mon., 10/20 | V Field Hockey | Stamford | Away - Stamford High School [Directions] | L 0-1 | PU:2:30 RE:6:30 | |
| Mon., 10/20 | JV Field Hockey | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Mon., 10/20 | FR Field Hockey | Stamford | Home - FLHS Front Lawn [Directions] | Cancelled | ||
| Mon., 10/20 | FR Girls Soccer | Staples | Home - Roger Ludlowe Middle School [Directions] | 4:00 p.m. | ||
| Mon., 10/20 | V Girls Swimming and Diving | Wilton | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/20 | V Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/20 | JV Girls Volleyball | Greenwich | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Mon., 10/20 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| Tue., 10/21 | V Girls Soccer | New Canaan | Home - Taft Field [Directions] | W 1-0 | ||
| Tue., 10/21 | JV Girls Soccer | New Canaan | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 10/21 | FR Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Wed., 10/22 | V Boys Soccer | Bassick | Away [Directions] | W 3-0 | PU:2:45 RE:5:30 | |
| Wed., 10/22 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 10/22 | V Field Hockey | Staples | Home - Taft Field [Directions] | L 0-4 | ||
| Wed., 10/22 | JV Field Hockey | Staples | Home - Taft Field [Directions] | 4:30 p.m. | ||
| Wed., 10/22 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | PU:2:45 RE:5:15 | |
| Wed., 10/22 | V Girls Swimming and Diving | Westhill/Stamford | Home - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/22 | V Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/22 | JV Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 5:45 p.m. | ||
| Wed., 10/22 | FR Girls Volleyball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 3:30 p.m. | PU:3:00 RE:5:30 | |
| Thu., 10/23 | FR Football | Westhill | Away - Rippowam Middle School - Turf Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 10/23 | V Girls Soccer | Brien McMahon | Home - Taft Field [Directions] | W 3-2 | ||
| Thu., 10/23 | JV Girls Soccer | Brien McMahon | Home - Sturges Park [Directions] | Cancelled | ||
| Fri., 10/24 | V Football | Westhill | Home - Taft Field [Directions] | L 12-24 2OT | ||
| Fri., 10/24 | V Boys Soccer | Wilton | Home - Taft Field [Directions] | W 2-0 | FCIAC Quarterfinals | |
| Fri., 10/24 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-1 | PU:2:30 RE:6:30 | |
| Fri., 10/24 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Sat., 10/25 | V Boys Cross Country | CIAC L Championships | Away | 12:00 p.m. | @ Wickham Park | |
| Sat., 10/25 | V Girls Cross Country | State LL Championship | Away | 1:00 p.m. | @ Wickham Park | |
| Mon., 10/27 | JV Football | Westhill | Away - Westhill HS [Directions] | 4:00 p.m. | ||
| Mon., 10/27 | V Boys Soccer | Norwalk | Home - Taft Field [Directions] | W 3-0 | FCIAC Semi-Finals | |
| Mon., 10/27 | V Boys Soccer | Norwalk | Home - Taft Field [Directions] | 7:00 p.m. | FCIAC Semi-Finals | |
| Tue., 10/28 | V Girls Volleyball | Ridgefield | Home - FLHS Main Gym [Directions] | W 3-0 | FCIAC Quarterfinals | |
| Wed., 10/29 | V Boys Soccer | Greenwich | Away - Norwalk HS [Directions] | W 1-0 | FCIAC Championship Game | |
| Thu., 10/30 | FR Football | Brien McMahon | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 10/30 | V Girls Volleyball | Trumbull | Home - FLHS Main Gym [Directions] | W 3-1 | FCIAC Sem-Finals | |
| Fri., 10/31 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | L 7-27 | PU:5:00 RE:8:30 | 2 Buses |
| Fri., 10/31 | V Competitive Cheerleading | Brien McMahon | Away [Directions] | 7:00 p.m. | PU:5:00 RE:8:30 | |
| Sat., 11/1 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:30 a.m. | PU:9:00 AM RE:12:00 | |
| Sat., 11/1 | V Girls Volleyball | Darien | Home - FLHS Main Gym [Directions] | L 0-3 | FCIAC Championship Game | |
| Tue., 11/4 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | L 1-2 | CIAC LL 1st Round | |
| Wed., 11/5 | V Boys Soccer | Glastonbury | Home - Taft Field [Directions] | 6:00 p.m. | States LL Second Round | |
| Thu., 11/6 | FR Football | East Haven | Home - Taft Field [Directions] | Cancelled | ||
| Thu., 11/6 | V Girls Volleyball | Glastonbury | Home - FLHS Main Gym [Directions] | W 3-1 | CIAC LL Second Round | |
| Fri., 11/7 | V Football | East Haven | Away - East Haven High School [Directions] | W 30-0 | PU:4:30 RE:8:30 | 2 Buses |
| Fri., 11/7 | V Competitive Cheerleading | East Haven | Away [Directions] | 7:00 p.m. | PU:5:15 RE:8:30 | |
| Sat., 11/8 | JV Football | East Haven | Away - East Haven High School [Directions] | 10:30 a.m. | PU:8:30am RE;12:00 | |
| Sat., 11/8 | V Girls Volleyball | Stamford | Home - FLHS Main Gym [Directions] | W 3-0 | CIAC LL Quarterfinals | |
| Thu., 11/13 | FR Football | Stamford | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 11/13 | V Girls Volleyball | Darien | Away - Shelton High School [Directions] | 6:00 p.m. | PU:4:00 RE:7:30 | CIAC LL Semi-Finals |
| Fri., 11/14 | V Football | Stamford | Away - Stamford High School [Directions] | L 17-35 | PU:4:00 RE:7:30 | 2 Buses |
| Fri., 11/14 | V Competitive Cheerleading | Stamford | Away [Directions] | 6:00 p.m. | PU:4:45 RE:7:30 | |
| Mon., 11/17 | JV Football | Fairfield Warde | Away [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Thu., 11/20 | FR Football | Fairfield Warde | Home - Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 11/27 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 12-27 | PU:8:15 RE:11:30 | 2 Buses |
| Thu., 11/27 | V Competitive Cheerleading | Fairfield Warde | Away [Directions] | 10:00 a.m. | PU:8:45 RE:11:30 | |
| Sat., 11/29 | V Girls Basketball | Notre Dame-Fairfield (Scrim.) | Away [Directions] | 9:00 a.m. | No Bus | |
| Tue., 12/2 | V Bowling | Notre Dame-Fairfield | Home - Nutmeg Lanes [Directions] | W 7-0 | ||
| Tue., 12/2 | JV Bowling | St. Joseph | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 12/2 | V Girls Basketball | Bunnell (Scrim.) | Home - FLHS Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 12/5 | V Boys Basketball | New Milford (Scrim.) | Home - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/6 | V Boys Ice Hockey | Woodstock Academy (Scrim.) | Away - Jahn Hockey Rink - Pomfret School [Directions] | 12:20 p.m. | PU 9:00am, RE 2:15PM | Jahn Rink (Pomfret School) |
| Sat., 12/6 | V Girls Basketball | Bethel (Scrim.) | Away [Directions] | 1:00 p.m. | PU:11:45 RE:2:45 | |
| Sat., 12/6 | V Girls Ice Hockey | Preseason Jamboree at Rinks at Shelton | Away | TBA | No Bus | |
| Mon., 12/8 | V Boys Basketball | Kolbe Cathedral (Scrim.) | Home - FLHS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/9 | V Bowling | Greenwich | Home - Nutmeg Lanes [Directions] | W 7-0 | ||
| Tue., 12/9 | JV Bowling | Stratford | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Wed., 12/10 | V Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | W 45-42 | PU3:30 RE:8:30 | |
| Wed., 12/10 | JV Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 12/10 | FR Girls Basketball | Wilton | Away - Wilton High School Field House [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 12/11 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell [Directions] | 5:30 p.m. | PU:4:15 RE:7:00 | |
| Fri., 12/12 | V Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | W 41-32 | PU:3:30 RE:8:30 | |
| Fri., 12/12 | JV Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 12/12 | FR Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Sat., 12/13 | V Boys Ice Hockey | Shelton Jamboree | Away | 6:30 p.m. | PU 5:15, RE 9:30 | Pick up at Wonderland of Ice |
| Sat., 12/13 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home [Directions] | 4:10 p.m. | ||
| Tue., 12/16 | V Bowling | Platt Tech | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 12/16 | JV Bowling | Platt Tech | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 12/16 | V Co-ed Fencing | Bridgeport Central | Away [Directions] | 6:30 p.m. | PU 5:30, RE 8:00 | |
| Wed., 12/17 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | W 69-44 | PUDO:4:00 REPU:8:30 | |
| Wed., 12/17 | JV Boys Basketball | St. Joseph | Away [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 12/17 | FR Boys Basketball | St. Joseph | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:00 | |
| Wed., 12/17 | V Boys Ice Hockey | Branford | Home - Wonderland Of Ice [Directions] | L 2-6 | ||
| Wed., 12/17 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | PU:2:30 RE:6:00 | |
| Wed., 12/17 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Auxiliary Gym [Directions] | Ludlowe 53 Harding 30 | PU:2:30 RE:5:30 | |
| Wed., 12/17 | V Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | L 35-48 | ||
| Wed., 12/17 | JV Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/17 | FR Girls Basketball | St. Joseph | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/17 | V Girls Ice Hockey | Greenwich | Home [Directions] | 3:30 p.m. | ||
| Fri., 12/19 | V Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | L 49-52 | ||
| Fri., 12/19 | JV Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Boys Basketball | Staples | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/19 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | PU:2:00 RE:5:00 | |
| Fri., 12/19 | V Co-ed Fencing | North Haven | Away [Directions] | 6:00 p.m. | PU 4:00, RE 8:00 | |
| Fri., 12/19 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 54-25 | PUDO:4:00 REPU:8:30 | |
| Fri., 12/19 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 12/19 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | PU:2:45 RE:5:30 | |
| Sat., 12/20 | V Wrestling | Ludlowe Invitational | Home - FLHS Main Gym [Directions] | 9:30 a.m. | WI: 7:30am Attending: Newtown, McMahon, Cheshire, Staples, Enfield, Windsor, Gethel, Harading, Prep, Central, Notre Dame | |
| Mon., 12/22 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | W 58-49 | PU:3:45 RE:8:30 | |
| Mon., 12/22 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Mon., 12/22 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 12/22 | V Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | L 48-61 | ||
| Mon., 12/22 | JV Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/22 | FR Girls Basketball | Greenwich | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/22 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 7:10 p.m. | PUFL:5:20 RE:8:40 | @ Ridgefield Rink |
| Tue., 12/23 | V Wrestling | Wilton | Home - FLHS Aux Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/26 | V Boys Basketball | Fairfield Prep | Away - Alumni Hall, Fairfield University [Directions] | L 63-71 | Prep Holiday Tourney | |
| Sat., 12/27 | V Boys Basketball | Fairfield Warde | Away [Directions] | W 62-53 | ||
| Sat., 12/27 | V Boys Ice Hockey | Danbury | Home - Wonderland Of Ice [Directions] | W 8-2 | ||
| Sat., 12/27 | V Wrestling | Glastonbury Duals | Away | 10:00 a.m. | PUDO:6:30am REPU:4:00pmpm | |
| Mon., 12/29 | JV Boys Basketball | Fairfield Prep | Home - FLHS Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 12/29 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | W 4-1 | PU 2:30, RE 5:30 | |
| Mon., 12/29 | V Girls Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | W 73-31 | ||
| Mon., 12/29 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 11:00 a.m. | No Bus | |
| Mon., 12/29 | V Girls Ice Hockey | Notre Dame-Fairfield | Away [Directions] | 8:00 p.m. | PUFL:6:00 RE:9:30 | @ Milford Ice Pavilion |
| Tue., 12/30 | V Wrestling | Danbury Quad | Away - Danbury High School | 9:00 a.m. | PU:7:00am RE:12:00pm | New Canaan Staples, Danbury |
| Tue., 12/30 | V Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | L 45-60 | ||
| Wed., 12/31 | JV Boys Basketball | Walter Fitzgerald Holiday Tourney | Home - FLHS Main Gym [Directions] | TBA | ||
| Sat., 1/3 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | W 4-3(OT) | PU 12:30, RE 3:30 | |
| Sat., 1/3 | V Boys Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | PUDO:8:00 am REPU:2:00 | Ridgefield, Darien, St. Joes, Warde Westhill |
| Sat., 1/3 | V Wrestling | Warde Tournament | Away | 9:30 a.m. | WI: 7:30 am Attending: RHAM, McMahon, NFA, Wilton, Prep, Westhill, Stamford, Mahopac, Simsbury, Montville | |
| Sat., 1/3 | V Co-ed Fencing | North Haven | Away [Directions] | 9:00 a.m. | PU 7:00, RE 4:00 | |
| Sat., 1/3 | V Girls Gymnastics | Pomperaug Invite | Away | 4th Place out of 11 | PUDO:7:00 am REPU:TBA | |
| Sat., 1/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home [Directions] | 3:00 p.m. | ||
| Sat., 1/3 | V Girls Indoor Track | Developmental Meet @ Wilton | Away | 9:30 a.m. | PUDO:8:00 am REPU:2:00 | Ridgefield, Darien, St. Joes, Warde Westhill |
| Mon., 1/5 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:30 p.m. | PUDO:5:00 No Return | |
| Mon., 1/5 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 2-6 | PU 6:30, RE 9:30 | |
| Mon., 1/5 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | FR Girls ride bus with FR Boys | |
| Mon., 1/5 | V Girls Ice Hockey | Daniel Hand Coop | Home [Directions] | 5:00 p.m. | ||
| Tue., 1/6 | V Boys Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | W 70-64 | ||
| Tue., 1/6 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | PU:2:45 RE:5:15 | |
| Tue., 1/6 | V Bowling | Fairfield Prep | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/6 | JV Bowling | Bunnell | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/6 | V Co-ed Fencing | Bridgeport Central | Home - Fairfield Warde Small Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/6 | V Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | L 34-57 | ||
| Tue., 1/6 | JV Girls Basketball | Fairfield Warde | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/7 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 1/7 | V Wrestling | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | PU:5:30 RE:8:30 | |
| Wed., 1/7 | V Girls Gymnastics | Fairfield Warde, Trumbull, Weston | Away - Gymnastics & Cheer Academy [Directions] | Ludlowe- 127.35, Trumbull- 127.65, Barlow- 99.75, Weston- 55.95 | ||
| Wed., 1/7 | V Girls Ice Hockey | New Canaan | Away [Directions] | 7:40 p.m. | PUFL:6:00 RE:9:00 | @ Darien Ice Rink |
| Thu., 1/8 | V Co-ed Alpine Skiing | Meet 1 | Away - Mt. Southington | TBA | PU FLHS 1:40, FWHS 1:50, RE 6:30 | Westhill (girls), Litchfield, Branford, Prep (boys), Greenwich, St. Lukes (boys) |
| Fri., 1/9 | V Boys Basketball | Bassick | Away [Directions] | L 55-65 | PU:4:15 RE:8:30 | |
| Fri., 1/9 | JV Boys Basketball | Bassick | Away [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 1/9 | FR Boys Basketball | Bassick | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 1/9 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | PU:2:00 RE:4:45 | |
| Sat., 1/10 | V Boys Ice Hockey | Trinity Catholic | Home - Wonderland of Ice [Directions] | W 10-1 | ||
| Sat., 1/10 | V Boys Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | PUDO:9:00 REPU: 2:00 | Ridgefield,Danbury, Stamford, Norwaslk, McMahon |
| Sat., 1/10 | V Wrestling | Xavier Duals | Away - Mercy High School | TBA | PUDO:6:30am REPU:4:00pm | |
| Sat., 1/10 | V Co-ed Fencing | Greens Farms Academy | Away | 9:00 a.m. | PU 7:30, RE 1:00 | |
| Sat., 1/10 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 7:30 p.m. | PUFL:5:45 RE:9:00 | @ Rinks at Shelton |
| Sat., 1/10 | V Girls Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | PUDO:9:00 REPU:2:00 | Trumbull, Ridgefield, Danbury, Stamford, Norwalk, McMahon |
| Mon., 1/12 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | L 1-2(OT) | PU 6:45, 10:00 | |
| Tue., 1/13 | V Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | W 62-34 | ||
| Tue., 1/13 | JV Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | Ridgefield | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/13 | V Bowling | Stratford | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/13 | JV Bowling | Greenwich | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/13 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 25-55 | PU:3:30 RE:8:30 | |
| Tue., 1/13 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Tue., 1/13 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | PU:2:30 RE:5:15 | |
| Tue., 1/13 | V Girls Gymnastics | Fairfield Warde, Darien | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 127.60, Darien- 128.85 | ||
| Wed., 1/14 | V Wrestling | Darien | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/14 | V Co-ed Fencing | Greens Farms Academy | Home - Fairfield Warde Small Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/14 | V Girls Ice Hockey | Darien | Home [Directions] | 5:00 p.m. | ||
| Thu., 1/15 | V Boys Swimming and Diving | New Canaan | Home - Fairfield University Rec Plex Pool [Directions] | 6:00 p.m. | ||
| Fri., 1/16 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | W 49-28 | PU:3:45 RE:8:30 | |
| Fri., 1/16 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | JV travels with Varsity | |
| Fri., 1/16 | FR Boys Basketball | Trinity Catholic | Away | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 1/16 | V Girls Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | W 67-20 | ||
| Fri., 1/16 | JV Girls Basketball | Trinity Catholic | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | FR Girls Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/16 | V Girls Ice Hockey | Notre Dame-Fairfield | Home [Directions] | 4:40 p.m. | ||
| Sat., 1/17 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | W 10-4 | PU 5:45, RE 9:30 | |
| Sat., 1/17 | V Boys Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | PUDO:9:00 REPU:2:00 | New Canaan, Greenwich, Warde, St. Joseph |
| Sat., 1/17 | V Wrestling | New Milford Tournament | Away | 9:00 a.m. | PU:6:30am REPU:5:00pm | |
| Sat., 1/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home [Directions] | 3:00 p.m. | ||
| Sat., 1/17 | V Girls Indoor Track | Developmental Meet at Staples | Away | 10:00 a.m. | PUDO:9:00 REPU:2:00 | Darien, New Canaan, Greenwich, Warde, St. Joseph |
| Mon., 1/19 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | Ludlowe- 134.90, Warde 76.25 | No Bus | |
| Tue., 1/20 | V Bowling | Bunnell | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/20 | JV Bowling | Bunnell | Home - Nutmeg Lanes [Directions] | Cancelled | ||
| Wed., 1/21 | V Boys Ice Hockey | Darien | Home - Wonderland Of Ice [Directions] | L 3-6 | ||
| Wed., 1/21 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 1/21 | V Wrestling | Greenwich | Home - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/21 | V Co-ed Alpine Skiing | Meet 2 | Away - Mt. Southington | TBA | PU FLHS 1:40, FWHS 1:50, RE 6:30 | Barlow, Weston, Farmington (boys), Girbert (boys), Ridgefield, Glastonbury, Westbrook (girls) |
| Wed., 1/21 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | 5:40 p.m. | PUFW:2:45 PUFL:3:00 RE:7:10 | @ Terry Connors |
| Thu., 1/22 | V Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | W 46-36 | ||
| Thu., 1/22 | JV Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/22 | FR Boys Basketball | Trumbull | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/22 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 38-55 | PUFR:2:30 PUJV/V:3:45 REPUFR:5:30 REJV/V:8:30 | |
| Thu., 1/22 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Thu., 1/22 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | Shuttle with JV/V | |
| Sat., 1/24 | V Boys Indoor Track | Developmental Meet @ Staples | Away | 10:00 a.m. | PUDO:9:00 REPU:2:00 | |
| Sat., 1/24 | V Wrestling | Rodney Smith Classic East Windsor | Away | 9:00 a.m. | PUDO:6:30am REPU:5:00pm | |
| Sat., 1/24 | V Girls Indoor Track | Developmental Meet at Staples | Away | 10:00 a.m. | PUDO:9:00 REPU:2:00 | Ridgefield, Darien, S.Joseph, Warde, Westhill |
| Tue., 1/27 | V Bowling | St. Joseph | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/27 | JV Bowling | Notre Dame-Fairfield | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 1/27 | V Co-ed Fencing | Daniel Hand | Home - Fairfield Warde Small Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/28 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 70-65(OT) | PU:3:45 RE:8:30 | |
| Wed., 1/28 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 1/28 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | PU5:30:2:30 RE: | |
| Wed., 1/28 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | W 5-1 | PU 3:00, RE 7:00 | |
| Wed., 1/28 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | PU:2:15 RE:5:30 | |
| Wed., 1/28 | V Co-ed Alpine Skiing | Meet 3 | Away - Mt. Southington | TBA | PU FLHS 1:40, FWHS 1:50, RE 6:30 | Amity, Chrshire, Staples, Laurelton (girls), Hopkins |
| Wed., 1/28 | V Co-ed Fencing | Staples | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/28 | V Girls Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | W 53-31 | ||
| Wed., 1/28 | JV Girls Basketball | Brien McMahon | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/28 | FR Girls Basketball | Wilton | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/29 | V Wrestling | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Thu., 1/29 | V Competitive Cheerleading | FCIAC Individuals | Home - FLHS Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/29 | V Co-ed Fencing | Morgan | Home - Fairfield Warde Small Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/30 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 49-36 | PU:3:45 RE:8:30 | |
| Fri., 1/30 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Fri., 1/30 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 1/30 | V Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | W 52-19 | ||
| Fri., 1/30 | JV Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/30 | FR Girls Basketball | New Canaan | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/31 | V Boys Ice Hockey | East Haven Coop | Home - Wonderland Of Ice [Directions] | W 2-0 | ||
| Sat., 1/31 | V Boys Indoor Track | FCIAC Central Championship | Away - Staples Fieldhouse | 10:00 a.m. | PUDO:9:00 AM REPU:2:00 PM | |
| Sat., 1/31 | V Wrestling | Ludlowe Classic Duals | Home - FLHS Main Gym [Directions] | 9:00 a.m. | WI:7:30 Attending: Norwalk, Imaculate-Barlow, Stratford, Conard, Notre Dame | |
| Sat., 1/31 | V Co-ed Fencing | Guilford | Away [Directions] | 10:00 a.m. | PU 7:00, RE 4:00 | |
| Sat., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | 11:50 a.m. | PUFL:10:20 RE:2:20 | @ SoNo Ice House |
| Sat., 1/31 | V Girls Indoor Track | Central Division Championship | Away - Staples Fieldhouse | 10:00 a.m. | PUDO:9:00 AM REPU:2:00 P | |
| Tue., 2/3 | V Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | W 68-57 | ||
| Tue., 2/3 | JV Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/3 | FR Boys Basketball | Bridgeport Central | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/3 | V Boys Swimming and Diving | Westhill/Stamford | Away [Directions] | 3:15 p.m. | PU:2:00 RE:4:45 | |
| Tue., 2/3 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 50-19 | PU:2:30 RE:6:45 | |
| Tue., 2/3 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | JV travels with Varsity | |
| Tue., 2/3 | V Girls Gymnastics | Wilton | Away - Wilton High School Aux. Gym [Directions] | Ludlowe- 136.30, Wilton 136.25 | PU:2:45 RE:6:00 | |
| Wed., 2/4 | V Boys Ice Hockey | Wilton | Home - Wonderland Of Ice [Directions] | W 5-0 | ||
| Wed., 2/4 | V Wrestling | Bridgeport Central | Away - Cafe [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 2/4 | V Girls Basketball | Bassick | Home - FLHS Main Gym [Directions] | W 53-20 | ||
| Thu., 2/5 | V Boys Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:30 p.m. | PUDO:2:30 REPU:TBA | |
| Thu., 2/5 | V Co-ed Alpine Skiing | Meet 4 | Away - Mt. Southington | TBA | PU FLHS 1:40, FWHS 1:50, RE 6:30 | Pomperaug, Wilton, Cheshire Academy (boys) |
| Thu., 2/5 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | PU:4:15 RE:7:30 | |
| Thu., 2/5 | V Girls Gymnastics | Westhill, New Canaan, Fairfield Warde | Away - Greenwich YWCA [Directions] | Ludlowe- 127.1, Greenwich- 128.0 | @ Westhill | |
| Thu., 2/5 | V Girls Ice Hockey | New Canaan | Home [Directions] | 4:40 p.m. | ||
| Thu., 2/5 | V Girls Indoor Track | FCIAC Championship @ Hillhouse | Away | 4:30 p.m. | Girls Travel with Boys Bus | |
| Fri., 2/6 | V Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | W 54-40 | ||
| Fri., 2/6 | JV Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/6 | FR Boys Basketball | Norwalk | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/6 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | PU:1:45 RE:4:30 | |
| Fri., 2/6 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 46-47(OT) | PU:2:30 RE:7:00 | |
| Fri., 2/6 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | JV travels with Varsity | |
| Fri., 2/6 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | PU:2:30 RE:5:15 | |
| Sat., 2/7 | V Boys Ice Hockey | Westhill/Stamford | Away [Directions] | W 2-0 | PU 1:30, RE 5:00 | |
| Sat., 2/7 | JV Wrestling | Matt Narwold JV Tourney | Home - FLHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/7 | V Competitive Cheerleading | FCIAC Championships | Away | 12:00 p.m. | ||
| Sat., 2/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Home [Directions] | 7:30 p.m. | ||
| Tue., 2/10 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | L 50-58 | PU:4:00 RE:8:30 | |
| Tue., 2/10 | JV Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Tue., 2/10 | FR Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 2/10 | V Boys Swimming and Diving | Fairfield Warde | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 2/10 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | PU:2:00 RE:5:30 | |
| Tue., 2/10 | V Wrestling | Staples | Away [Directions] | Cancelled | PU:4:30 RE:7:00 | |
| Tue., 2/10 | V Bowling | Kolbe Cathedral | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 2/10 | JV Bowling | Fairfield Prep | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 2/10 | V Co-ed Fencing | Greens Farms Academy | Away | 4:00 p.m. | PU 3:00, RE 5:30 | |
| Tue., 2/10 | V Girls Basketball | Harding | Home - FLHS Main Gym [Directions] | W 58-9 | ||
| Tue., 2/10 | JV Girls Basketball | Harding | Home - FLHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/10 | V Girls Gymnastics | Staples, Fairfield Warde | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 127.25, Staples- 116.65 | ||
| Wed., 2/11 | V Boys Ice Hockey | Trumbull | Home [Directions] | W 4-2 | ||
| Wed., 2/11 | V Girls Ice Hockey | Darien | Away [Directions] | 7:40 p.m. | PUFL:6:00 RE:9:00 | @ Darien Ice Rink |
| Thu., 2/12 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 1-5 | PU FLHS 2pm, FWHS 2:15, RE 5:30 | |
| Thu., 2/12 | V Co-ed Alpine Skiing | Meet 5 | Away - Mt. Southington | TBA | PU FLHS 1:40, FWHS 1:50, RE 6:30 | Guilford, Darien, Southington, New Canaan (boys), Danbury |
| Thu., 2/12 | V Bowling | Joel Barlow | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Thu., 2/12 | JV Bowling | Kolbe Cathedral | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Fri., 2/13 | V Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | W 62-51 | ||
| Fri., 2/13 | JV Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/13 | FR Boys Basketball | Darien | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/13 | V Boys Indoor Track | CIAC State Meet | Away - Hillhouse HS | 4:00 p.m. | ||
| Fri., 2/13 | V Wrestling | FCIAC's | Away | 4:30 p.m. | PUDO:2:30 No Return | @ New Canaan |
| Fri., 2/13 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | L 44-51 | PU:2:30 RE:7:00 | |
| Fri., 2/13 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | JV travels with Varsity | |
| Sat., 2/14 | V Wrestling | FCIAC's | Away | 10:00 a.m. | @ New Canaan | |
| Sat., 2/14 | V Girls Gymnastics | FCIAC Championship | Away - Jonathan Law HS | 3rd Place | PUDOFL: 8:45 am | @ Jonathan Law HS |
| Sat., 2/14 | V Girls Gymnastics | FCIAC Championships | Away - Jonathan Law HS | 11:00 a.m. | ||
| Sat., 2/14 | V Girls Indoor Track | CIAC State Meet | Away - Hillhouse HS | 4:30 p.m. | PU:1:00 RE:7;30 | |
| Mon., 2/16 | V Boys Basketball | Stamford | Away [Directions] | W 61-55 | PU:3:45 RE:8:30 | |
| Mon., 2/16 | JV Boys Basketball | Stamford | Away [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Mon., 2/16 | FR Boys Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Mon., 2/16 | V Boys Ice Hockey | Greenwich | Home - Wonderland Of Ice [Directions] | L 1-2 | ||
| Mon., 2/16 | V Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | L 41-47 | ||
| Mon., 2/16 | JV Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/16 | FR Girls Basketball | Stamford | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/16 | V Girls Ice Hockey | Greenwich | Away [Directions] | 5:45 p.m. | PUFL:3:45 RE:7:00 | @ Dorothy Hamill |
| Wed., 2/18 | V Boys Basketball | Westhill | Away [Directions] | L 38-61 | PU:3:30 RE:8:30 | |
| Wed., 2/18 | JV Boys Basketball | Westhill | Away [Directions] | 5:15 p.m. | JV travels with Varsity | |
| Wed., 2/18 | FR Boys Basketball | Westhill | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 2/18 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | W 2-1(OT) | PU 3:45, RE 7:30 | |
| Wed., 2/18 | V Girls Basketball | Westhill | Home - FLHS Main Gym [Directions] | W 54-45 | ||
| Wed., 2/18 | JV Girls Basketball | Westhill | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/18 | FR Girls Basketball | Westhill | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/18 | V Girls Gymnastics | Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | Ludlowe 131.45, Daniel Hand 135.55 | PU:3:30 RE:7:30 | |
| Thu., 2/19 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Flood Middle School [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Fri., 2/20 | V Wrestling | CIAC Class L States | Away | TBA | @ Bristol Central | |
| Fri., 2/20 | V Girls Gymnastics | Foran | Home - Gymanstics and Cheer Academy [Directions] | Ludlowe- 130.2, Foran- 102.75 | ||
| Sat., 2/21 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | W 1-0 | PU 11:15, RE 2:30 | |
| Sat., 2/21 | V Boys Indoor Track | CIAC Open | Away - Hillhouse HS | 12:00 p.m. | ||
| Sat., 2/21 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/21 | V Girls Basketball | Wilton | Away - Fairfield Warde Main Gym [Directions] | L 32-73 | FCIAC Quarterfinals | |
| Sat., 2/21 | V Girls Indoor Track | CIAC Open | Away - Hillhouse HS | 12:00 p.m. | ||
| Sat., 2/21 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/23 | V Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | W 56-40 | ||
| Mon., 2/23 | JV Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/23 | FR Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/23 | V Boys Ice Hockey | Cheshire | Home - Wonderland Of Ice [Directions] | W 4-2 | ||
| Mon., 2/23 | V Co-ed Fencing | North Haven | Home - Fairfield Warde Small Gym [Directions] | 6:00 p.m. | Senior Night | |
| Tue., 2/24 | V Boys Swimming and Diving | FCIAC Trials | Away | 4:30 p.m. | PUDOFW:2:20 FL:2:35 REPU:8:00 | |
| Tue., 2/24 | V Bowling | Notre Dame-Fairfield | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Tue., 2/24 | JV Bowling | St. Joseph | Home - Nutmeg Lanes [Directions] | 3:30 p.m. | ||
| Wed., 2/25 | V Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | W 56-40 | ||
| Wed., 2/25 | JV Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/25 | FR Boys Basketball | Danbury | Home - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/25 | V Boys Ice Hockey | Staples | Home - Wonderland Of Ice [Directions] | W 7-1 | ||
| Thu., 2/26 | V Boys Swimming and Diving | FCIAC Championship | Away | 6:30 p.m. | ||
| Thu., 2/26 | V Co-ed Alpine Skiing | Practice | Away - Mt. Southington | 3:00 p.m. | PU FLHS 2:15, PU FWHS 2:30 | |
| Thu., 2/26 | V Co-ed Fencing | Guilford | Away [Directions] | 6:00 p.m. | PU 4:00, RE 8:00 | |
| Fri., 2/27 | V Wrestling | CIAC State Open | Away | TBA | @ Hillhouse | |
| Sat., 2/28 | V Boys Basketball | Wilton | Home - FLHS Main Gym [Directions] | 2:00 p.m. | FCIAC Quarterfinals | |
| Sat., 2/28 | V Co-ed Fencing | Greenwich | Away [Directions] | 9:00 a.m. | PU 8:00, RE 2:00 | also Greenwich, Guilford |
| Sat., 2/28 | V Girls Gymnastics | State Championships | Away - Pomperaug HS | 1:30 p.m. | ||
| Wed., 3/4 | V Girls Basketball | Nonnewaug | Away [Directions] | W 51-42 | PU:2:30 RE:7:00 | CIAC LL First Round |
| Fri., 3/6 | V Girls Basketball | E.O. Smith | Away - E.O. Smith HS [Directions] | W 41-37 | PU:2:15 RE:7:30 | CIAC LL Second Round |
| Sat., 3/7 | V Co-ed Fencing | Hopkins School | Away | 9:00 a.m. | PU 7:00, RE 5:00 | State Championships |
| Sat., 3/7 | V Girls Gymnastics | State Open | Away - New Milford HS | 10:30 a.m. | ||
| Sun., 3/8 | V Girls Gymnastics | Ro Carlucci JV Meet | Home - Gymnastics Cheer Academy [Directions] | 4:00 p.m. | ||
| Mon., 3/9 | V Boys Basketball | New Britain | Home - FLHS Main Gym [Directions] | W 60-49 | CIAC LL First Round | |
| Mon., 3/9 | V Co-ed Alpine Skiing | State Championship | Away | 2:00 p.m. | PU FLHS 10:15, FWHS 10:40, RE 4:30 | |
| Tue., 3/10 | V Boys Ice Hockey | Milford Coop | Home - Wonderland Of Ice [Directions] | W 4-1 | ||
| Tue., 3/10 | V Girls Basketball | Mercy | Away - Mercy [Directions] | 7:00 p.m. | PU:4:00 RE:8:30 | CIAC LL Quarterfinals |
| Wed., 3/11 | V Boys Basketball | Hamden | Home - FLHS Main Gym [Directions] | 7:00 p.m. | CIAC LL Second Round | |
| Fri., 3/13 | V Boys Basketball | Fairfield Prep | Away - Alumni Hall, Fairfield University [Directions] | 7:00 p.m. | CIAC LL Quarterfinals | |
| Fri., 3/13 | V Boys Ice Hockey | Branford | Away [Directions] | 7:00 p.m. | PU 5:15, RE 8:45 | at Milford Ice Pavilion |
| Sat., 3/14 | V Co-ed Fencing | State Tournament at Bridgeport Central HS | Away | 9:00 a.m. | PU 7:30, RE 3:00 | at Bridgeport Central HS |
| Wed., 3/18 | Unified Sports Basketball | Jack Title Unifiedl Basketball Tournament | Home - FLHS Main Gym [Directions] | 3:00 p.m. | Fairfield Ludlowe Hosts | |
| Fri., 3/27 | V Boys Lacrosse | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 5:30 p.m. | PU:3:30 RE:6:45 | |
| Sat., 3/28 | V Girls Lacrosse | Danbury (Scrim.) | Away [Directions] | 9:00 a.m. | PU:7:30am RE:12:00 | |
| Tue., 3/31 | V Baseball | Fairfield Prep (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/1 | V Baseball | Fairfield Warde (Scrim.) | Home - Kiwanis Field [Directions] | 3:45 p.m. | ||
| Wed., 4/1 | JV Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 3:45 p.m. | ||
| Wed., 4/1 | FR Baseball | Fairfield Warde (Scrim.) | Home - Owen Fish Park [Directions] | 3:45 p.m. | ||
| Wed., 4/1 | V Boys Lacrosse | Guilford (Scrim.) | Away - Kavanaugh Turf Field at GHS [Directions] | 6:00 p.m. | PU:3:45 RE:7:45 | |
| Wed., 4/1 | V Co-ed Sailing | Greenwich | Away - Grassy Island [Directions] | 3:00 p.m. | PUFW: 2:20 PUFL:2:35 RE:5:00 | with Rye Country Day |
| Thu., 4/2 | V Baseball | Naugatuck (Scrim.) | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Thu., 4/2 | V Girls Lacrosse | Danbury (Scrim.) | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 4/4 | V Baseball | Weston (Scrim.) | Home - Kiwanis Field [Directions] | 10:00 a.m. | ||
| Sat., 4/4 | V Baseball | Pomperaug (Scrim.) | Away - Weston HS [Directions] | 12:30 p.m. | ||
| Sat., 4/4 | V Boys Lacrosse | Trumbull (Scrim.) | Home - Taft Field [Directions] | 9:00 a.m. | ||
| Sat., 4/4 | V Girls Lacrosse | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 10:00 a.m. | PU:8:00 am RE:12:00 | |
| Mon., 4/6 | V Softball | Weston (Scrim.) | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 4/8 | V Boys Lacrosse | Xavier | Home - Rafferty Stadium at Fairfield University [Directions] | W 6-5(OT) | ||
| Wed., 4/8 | JV Boys Lacrosse | Xavier | Home - Rafferty Stadium at Fairfield Universtiy [Directions] | 4:30 p.m. | ||
| Wed., 4/8 | FR Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | PU:3:00 RE:6:00 | |
| Wed., 4/8 | V Co-ed Sailing | Brunswick School | Away - Indian Harbor YC | 3:00 p.m. | PUFL:2:25 RE:5:00 | with Mamaroneck, Rye |
| Wed., 4/8 | V Girls Lacrosse | Darien | Home - Taft Field [Directions] | L 5-11 | ||
| Wed., 4/8 | JV Girls Lacrosse | Darien | Home - Taft Field [Directions] | 5:15 p.m. | ||
| Wed., 4/8 | V Softball | Masuk | Home - Sturges Park [Directions] | W 8-7 | ||
| Wed., 4/8 | V Girls Tennis | Westhill | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/9 | V Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | L 5-6 | PU:2:30 RE:5:45 | |
| Thu., 4/9 | JV Baseball | Newtown | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | FR Baseball | Newtown | Home - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | V Boys Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 4-3 | ||
| Thu., 4/9 | JV Boys Tennis | Darien | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/9 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 4/10 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 4/10 | V Softball | St. Joseph | Home - Sturges Park [Directions] | L 1-5 | ||
| Fri., 4/10 | JV Softball | St. Joseph | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Sat., 4/11 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | L 16-21 | PU:1:30 RE:5:00 | |
| Sat., 4/11 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | W 10-9(OT) | PU:12:00 RE:3:30 | |
| Sat., 4/11 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 12:00 p.m. | PU:10:15 RE:1:30 | |
| Sat., 4/11 | V Girls Lacrosse | Staples | Home - Taft Field [Directions] | L 12-13 OT | ||
| Sat., 4/11 | JV Girls Lacrosse | Staples | Home - Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 4/11 | V Girls Tennis | Weston | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/13 | V Baseball | Staples | Home - Kiwanis Field [Directions] | L 0-12 | ||
| Mon., 4/13 | JV Baseball | Staples | Home - Tunxis Hill Park [Directions] | 12:00 p.m. | ||
| Mon., 4/13 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 12:00 p.m. | PU:10:30 RE:1:30 | |
| Mon., 4/13 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | PU:3:30 RE:6:30 | |
| Mon., 4/13 | V Boys Tennis | New Canaan | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Mon., 4/13 | V Girls Lacrosse | Nauset Regional (MA) | Away | W 15-10 | Non League | |
| Mon., 4/13 | V Softball | Staples | Away - Wakeman Field [Directions] | W 7-0 | PU:9:30 RE:12:30 | |
| Mon., 4/13 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Tue., 4/14 | V Boys Lacrosse | Ridgefield | Home - Taft Field [Directions] | L 3-15 | ||
| Tue., 4/14 | JV Boys Lacrosse | Ridgefield | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 4/14 | V Boys Tennis | Brien McMahon | Home - Lundlowe [Directions] | W 6-1 | PU:9:45 am RE:12:00 | |
| Tue., 4/14 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | W 9-4 | PU:2:30 RE:6:00 | |
| Tue., 4/14 | V Girls Tennis | Brien McMahon | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/15 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | W 4-3 | PU:2:30 RE:5:45 | |
| Wed., 4/15 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 1:00 p.m. | JV Travels with Varsity | |
| Wed., 4/15 | FR Baseball | Greenwich | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Wed., 4/15 | V Girls Lacrosse | Stamford | Home - Taft Field [Directions] | W 17-8 | ||
| Wed., 4/15 | JV Girls Lacrosse | Stamford | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 4/15 | V Softball | Greenwich | Home - Sturges Park [Directions] | W 4-0 | ||
| Wed., 4/15 | JV Softball | Greenwich | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Thu., 4/16 | V Boys Lacrosse | Conard | Away - Conard HS Stadium [Directions] | W 13-4 | PU:2:30 RE:6:30 | |
| Thu., 4/16 | JV Boys Lacrosse | Conard | Away - Conard HS Stadium [Directions] | 3:00 p.m. | PU:1:00 RE:4:30 | |
| Thu., 4/16 | FR Boys Lacrosse | Trumbull | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Fri., 4/17 | V Baseball | Fairfield Warde | Home - Harbor Yard [Directions] | L 3-4 | PU:4:30 RE:8:00 | |
| Fri., 4/17 | JV Baseball | Fairfield Warde | Home - Kiwanis Field [Directions] | 1:00 p.m. | ||
| Fri., 4/17 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 0-2 | PU:11:45 RE:2:30 | |
| Fri., 4/17 | JV Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:00 p.m. | JV Travels with Varsity | |
| Sat., 4/18 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 10-14 | PU: 4:00 RE:8:30 | |
| Sat., 4/18 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:00 p.m. | JV Travels with Varsity | |
| Tue., 4/21 | V Baseball | Bassick | Away [Directions] | W 28-0 | PU:2:30 RE:6:00 | |
| Tue., 4/21 | FR Baseball | Fairfield Warde | Away - Owen Fish [Directions] | 3:30 p.m. | No Bus | |
| Tue., 4/21 | V Boys Golf | Staples | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 166 Staples: 170 | ||
| Tue., 4/21 | V Boys Lacrosse | Darien | Home - Taft Field [Directions] | L 5-13 | ||
| Tue., 4/21 | JV Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Tue., 4/21 | V Girls Golf | Trumbull | Home - Smith Richardson Golf Course [Directions] | Trumbull 227 Ludlowe 232 | ||
| Tue., 4/21 | JV Girls Golf | Greenwich | Home [Directions] | 3:30 p.m. | ||
| Tue., 4/21 | V Girls Lacrosse | Ridgefield | Home - Taft Field [Directions] | W 10-8 | ||
| Tue., 4/21 | JV Girls Lacrosse | Ridgefield | Home - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Girls Tennis | Trumbull | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/22 | JV Boys Golf | Darien, Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | Cancelled | ||
| Wed., 4/22 | V Girls Golf | Greenwich | Home - Smith Richardson Golf Course [Directions] | Greenwich 183 Ludlowe 226 | ||
| Wed., 4/22 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | W 4-2 | PU:2:30 RE:2:30 | |
| Thu., 4/23 | V Baseball | Ridgefield | Home - Kiwanis Field [Directions] | L 3-8 | ||
| Thu., 4/23 | JV Baseball | Ridgefield | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 4/23 | V Boys Golf | Westhill, Stamford | Away - E. Gaynor Brennan [Directions] | Ludlowe: 166 Westhill: 176 Stamford: 220 | PU:2:10 RE:5:30 | |
| Thu., 4/23 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | W 7-6(OT) | PU:5:15 RE:8:30 | |
| Thu., 4/23 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 5:00 p.m. | PU:2:30 RE;5:30 | |
| Thu., 4/23 | V Boys Tennis | Staples | Home - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | ||
| Thu., 4/23 | JV Boys Tennis | Staples | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/23 | V Co-ed Sailing | Staples | Home - Pequot YC [Directions] | 3:00 p.m. | with Stamford, Mamaroneck | |
| Thu., 4/23 | V Girls Outdoor Track | Greenwich, Ridgefield | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 4/23 | V Softball | Bassick | Home - Sturges Park [Directions] | W 12-0 | ||
| Thu., 4/23 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | W 4-3 | PU:2:30 RE:5:30 | |
| Thu., 4/23 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 4/24 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | L 1-2 | PU:2:30 RE:5:45 | |
| Fri., 4/24 | JV Baseball | Trinity Catholic | Away - Barrett Field @ Belltown Park | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 4/24 | FR Baseball | Trinity Catholic | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | V Boys Tennis | Westhill | Away [Directions] | W 6-1 | PU:2:30 RE:5:30 | |
| Fri., 4/24 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 19-5 | PU:2:30 RE:5:30 | Non League |
| Fri., 4/24 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Fri., 4/24 | V Softball | Trinity Catholic | Home - Sturges Park [Directions] | W 8-5 | ||
| Fri., 4/24 | V Girls Tennis | Danbury | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/25 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | W 14-7 | PU:2:30 RE:5:30 | |
| Sat., 4/25 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | PU:3:45 RE:6:45 | |
| Mon., 4/27 | FR Baseball | Fairfield Prep | Away - Owen Fish [Directions] | 3:45 p.m. | ||
| Mon., 4/27 | V Boys Golf | Ridgefield | Home - Smith Richardson Golf Course [Directions] | Ridgefield: 161 Ludlowe: 176 | ||
| Mon., 4/27 | V Boys Lacrosse | Southington | Home - Taft Field [Directions] | W 10-3 | ||
| Mon., 4/27 | JV Boys Lacrosse | Southington | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Mon., 4/27 | FR Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | PU:4:30 RE:7:30 | |
| Mon., 4/27 | V Boys Tennis | St. Joseph | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/27 | V Girls Outdoor Track | Norwalk, Brien McMahon | Away - Testa Field, NHS [Directions] | 3:45 p.m. | PU:2:20 RE:5:45 | 2 Buses |
| Mon., 4/27 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | W 7-0 | PU:2:30 RE:5:30 | |
| Tue., 4/28 | V Baseball | Northwestern | Home - Kiwanis Field [Directions] | W 13-12 | ||
| Tue., 4/28 | JV Baseball | Northwestern | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Tue., 4/28 | V Boys Golf | Trinity Catholic | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 168 Trinity Catholic: 192 | ||
| Tue., 4/28 | JV Boys Golf | Fairfield Warde, Fairfield Prep | Home - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/28 | V Boys Outdoor Track | Brien McMahon, Norwalk | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Tue., 4/28 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | PU:2:30 RE:5:30 | |
| Tue., 4/28 | JV Boys Tennis | Greenwich | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/28 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | Wilton 191 Ludlowe 196 | PU:2:00 RE:5:30 | |
| Tue., 4/28 | JV Girls Golf | Trumbull | Home [Directions] | 3:30 p.m. | ||
| Tue., 4/28 | V Girls Lacrosse | Amity | Away - Amity High School - Field # 3 [Directions] | W 20-5 | PU:2:00 RE:5:15 | Non League |
| Tue., 4/28 | JV Girls Lacrosse | Amity | Away - Amity High School - Field # 3 [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Tue., 4/28 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | L 2-3 | PU:2:20 RE:5:30 | |
| Tue., 4/28 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Tue., 4/28 | V Girls Tennis | Trinity Catholic | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Tue., 4/28 | JV Girls Tennis | Greenwich | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | V Baseball | Trumbull | Home - Kiwanis Field [Directions] | L 3-6 | ||
| Wed., 4/29 | JV Baseball | Trumbull | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 4/29 | V Boys Golf | Trumbull | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 172 Trumbull: 175 | ||
| Wed., 4/29 | FR Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 4/29 | V Boys Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | W 7-0 | PU:2:20 RE:5:30 | |
| Wed., 4/29 | V Co-ed Sailing | Greenwich Academy | Away - Indian Harbor YC | 3:00 p.m. | PUFL:2:25 RE:5:00 | with Staples |
| Wed., 4/29 | V Girls Golf | New Canaan | Home - Smith Richardson Golf Course [Directions] | Ludlowe 220 New Canaan 226 | ||
| Wed., 4/29 | JV Girls Golf | Staples | Home [Directions] | 3:30 p.m. | ||
| Wed., 4/29 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 0-3 | PU:2:30 RE:5:30 | |
| Wed., 4/29 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 4/30 | V Boys Golf | Darien | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 161 Darien: 169 | ||
| Thu., 4/30 | V Boys Outdoor Track | Greenwich, Ridgefield | Away - Cardinal Stadium [Directions] | 4:00 p.m. | PU:2:10 RE:6:00 | 2 Buses |
| Thu., 4/30 | V Boys Tennis | Wilton | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/30 | JV Boys Tennis | Wilton | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/30 | V Girls Golf | Ridgefield, Fairfield Warde | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Warde 177 Ridgefield 180 Ludlowe 219 | PU:1:45 RE:5:15 | |
| Thu., 4/30 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 15-5 | PU:3:30 RE:6:45 | |
| Thu., 4/30 | JV Girls Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 5:00 p.m. | JV Travels with Varsity | |
| Thu., 4/30 | V Girls Tennis | Wilton | Away - Tennis Courts [Directions] | W 4-3 | PU:2:30 RE:5:30 | |
| Thu., 4/30 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 5/1 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 2-4 | PU:2:30 RE:5;30 | |
| Fri., 5/1 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 5/1 | FR Baseball | Brien McMahon | Home - Kiwanis Field [Directions] | Cancelled | ||
| Fri., 5/1 | V Boys Lacrosse | Trinity Catholic | Home - Taft Field [Directions] | W 15-1 | ||
| Fri., 5/1 | JV Boys Lacrosse | Bridgeport Central | Home - Taft Field [Directions] | Cancelled | ||
| Fri., 5/1 | FR Boys Lacrosse | Ridgefield | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Fri., 5/1 | V Softball | Brien McMahon | Home - Sturges Park [Directions] | W 4-1 | ||
| Fri., 5/1 | JV Softball | Brien McMahon | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Sat., 5/2 | V Boys Lacrosse | Brien McMahon | Home - Taft Field [Directions] | W 15-10 | ||
| Sat., 5/2 | JV Boys Lacrosse | Brien McMahon | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Sat., 5/2 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 20-10 | PU:2:00 RE:6:00 | |
| Sat., 5/2 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 3:30 p.m. | JV Travels with Varsity | |
| Mon., 5/4 | V Baseball | New Canaan | Away - Mead Park [Directions] | L 1-5 | PU:2:30 RE:5:30 | |
| Mon., 5/4 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Mon., 5/4 | FR Baseball | New Canaan | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Boys Golf | Harding, Bridgeport Central | Away [Directions] | Ludlowe: 164 Harding: 248 Central: 272 | PU:2:20 RE:5:30 | |
| Mon., 5/4 | V Boys Tennis | Fairfield Warde | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/4 | JV Boys Tennis | Fairfield Warde | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Warde - 192 Ludlowe - 219 | ||
| Mon., 5/4 | V Girls Lacrosse | Wilton | Home - Taft Field [Directions] | W 14-13 | ||
| Mon., 5/4 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | PU:2:30 RE:5:15 | |
| Mon., 5/4 | V Girls Outdoor Track | Bridgeport Central, Trumbull | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Softball | New Canaan | Home - Sturges Park [Directions] | W 17-9 | ||
| Mon., 5/4 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 5-2 | PU:2:30 RE:6:00 | |
| Mon., 5/4 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods Middle School Courts [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Tue., 5/5 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 13-6 | PUJV:3:30 PUVAR:5:30 REJV:6:45 REVAR:8:30 | |
| Tue., 5/5 | JV Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:00 p.m. | Shuttle with Var | |
| Tue., 5/5 | V Boys Outdoor Track | Trumbull, Bridgeport Central | Away - McDougall Stadium [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 Buses |
| Tue., 5/5 | V Co-ed Sailing | Greenwich Academy | Away - Indian Harbor YC | 3:00 p.m. | PUFL:2:25 RE:5:00 | Womans Championships |
| Tue., 5/5 | V Girls Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | Ludlowe 224 Wilton 244 | ||
| Tue., 5/5 | JV Girls Golf | Greenwich | Home [Directions] | 3:30 p.m. | ||
| Wed., 5/6 | V Baseball | Bridgeport Central | Home - Kiwanis Field [Directions] | W 17-8 | ||
| Wed., 5/6 | JV Baseball | Bridgeport Central | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/6 | FR Baseball | Fairfield Country Day School | Away | 3:30 p.m. | PUDO Only: 2:30 | No Return Bus |
| Wed., 5/6 | V Boys Golf | Wilton | Home - Smith Richardson Golf Course [Directions] | Wilton: 163 Ludlowe: 170 | ||
| Wed., 5/6 | FR Boys Lacrosse | Fairfield Prep | Home - Sturges Park [Directions] | 3:45 p.m. | ||
| Wed., 5/6 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 3:45 p.m. | PUDO Only:2:30 | |
| Wed., 5/6 | V Co-ed Sailing | Greenwich | Away - Grass Island [Directions] | 3:00 p.m. | PUFL:2:25 RE:5:00 | with Darien, Stamford |
| Wed., 5/6 | FR Girls Lacrosse | Trumbull | Home - FLHS Front Field [Directions] | Cancelled | ||
| Wed., 5/6 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 14-3 | PU:2:30 RE:5:30 | |
| Wed., 5/6 | JV Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Wed., 5/6 | JV Girls Tennis | New Canaan | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 5/7 | V Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | Ludlowe: 170 Brien McMahon: 196 | PU:2:20 RE:5:30 | |
| Thu., 5/7 | V Boys Tennis | Stamford | Away [Directions] | W 7-0 | PU:2:30 RE:5:30 | |
| Thu., 5/7 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | Darien: 202 Ludlowe: 239 | PU:2:05 RE:5:30 | |
| Thu., 5/7 | JV Girls Golf | Staples | Home [Directions] | 3:30 p.m. | ||
| Thu., 5/7 | V Girls Tennis | Stamford | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Fri., 5/8 | V Baseball | Norwalk | Home - Kiwanis Field [Directions] | L 1-3 | ||
| Fri., 5/8 | JV Baseball | Norwalk | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | FR Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Fri., 5/8 | FR Boys Lacrosse | Wilton | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | V Boys Outdoor Track | Fairfield Warde, Bassick, Harding | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Fri., 5/8 | V Girls Outdoor Track | Fairfield Warde, Harding, Bassick | Home - Taft Field [Directions] | 3:45 p.m. | ||
| Fri., 5/8 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | L 2-4 | PU:2:30 RE:5:30 | |
| Fri., 5/8 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 5/8 | JV Girls Tennis | Staples | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/9 | V Boys Lacrosse | Norwalk | Home - Taft Field [Directions] | W 13-4 | ||
| Sat., 5/9 | JV Boys Lacrosse | Norwalk | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 5/9 | V Co-ed Sailing | Greenwich | Away [Directions] | 9:00 a.m. | PUDO: 7:45 REPU:4:00 | @ IHYC |
| Sat., 5/9 | V Girls Lacrosse | Joel Barlow | Home - Taft Field [Directions] | L 7-8 | Non League | |
| Sat., 5/9 | JV Girls Lacrosse | Joel Barlow | Home - Taft Field [Directions] | 10:15 a.m. | ||
| Sun., 5/10 | V Co-ed Sailing | Fairfield Cup | Away | 10:00 a.m. | ||
| Mon., 5/11 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | W 19-4 | PU:2:30 RE:5:30 | |
| Mon., 5/11 | JV Baseball | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Mon., 5/11 | FR Boys Lacrosse | Fairfield Country Day School | Away | 3:30 p.m. | PUDO: 2:30 | No Return Bus |
| Mon., 5/11 | V Boys Tennis | Ridgefield | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/11 | JV Boys Tennis | Ridgefield | Home - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Girls Golf | Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | Warde: 202 Ludlowe: 243 | ||
| Mon., 5/11 | V Girls Lacrosse | Brien McMahon | Home - Taft Field [Directions] | W 20-5 | ||
| Mon., 5/11 | JV Girls Lacrosse | Brien McMahon | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 5/11 | V Girls Outdoor Track | New Canaan, Staples | Away - NCHS Track Field [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 Buses |
| Mon., 5/11 | V Softball | Harding | Home - Sturges Park [Directions] | W 12-0 | ||
| Mon., 5/11 | JV Softball | Harding | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 5-2 | PU:2:30 RE:5:30 | |
| Mon., 5/11 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Tue., 5/12 | V Boys Golf | St. Joseph | Away - Tashua Knolls, Trumbull [Directions] | Ludlowe: 164 St. Joseph: 194 | PU:2:20 RE:5:30 | |
| Tue., 5/12 | JV Boys Golf | Greenwich | Home - Smith Richardson Golf Course [Directions] | 3:20 p.m. | ||
| Tue., 5/12 | V Boys Lacrosse | New Canaan | Home - Taft Field [Directions] | L 8-11 | ||
| Tue., 5/12 | JV Boys Lacrosse | New Canaan | Home - Sturges Park [Directions] | 5:00 p.m. | ||
| Tue., 5/12 | V Boys Outdoor Track | Staples, New Canaan | Away - Staples Stadium [Directions] | 4:00 p.m. | PU:2:30 RE:6:00 | 2 Buses |
| Tue., 5/12 | V Boys Tennis | Norwalk | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/12 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | New Canaan: 220 Ludlowe: 240 | PU:2:10 RE:5:15 | |
| Tue., 5/12 | V Girls Tennis | Norwalk | Away - Norwalk High School [Directions] | W 7-0 | PU:2:30 RE:5:30 | |
| Wed., 5/13 | V Baseball | Darien | Home - Kiwanis Field [Directions] | L 2-5 | ||
| Wed., 5/13 | JV Baseball | Darien | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 5/13 | V Boys Golf | Greenwich | Home - Smith Richardson Golf Course [Directions] | Greenwich: 162 Ludlowe: 168 | ||
| Wed., 5/13 | JV Boys Golf | Darien, Fairfield Warde | Home - Smith Richardson Golf Course [Directions] | 3:40 p.m. | ||
| Wed., 5/13 | FR Boys Lacrosse | Trumbull | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | JV Boys Tennis | Fairfield Warde | Home - Dwight Elementary School Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/13 | V Co-ed Sailing | Greenwich Academy | Away - Indian Harbor YC | 3:00 p.m. | PUFL:2:25 RE:5:00 | with Brunswick, Rye Country Day |
| Wed., 5/13 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | L 1-6 | PU:2:30 RE:5:30 | |
| Wed., 5/13 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Wed., 5/13 | JV Girls Tennis | Fairfield Warde | Home - Tomlinson MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/14 | V Baseball | Stamford | Away - Stamford High School [Directions] | W 4-2 | PU:2:30 RE:6:00 | |
| Thu., 5/14 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 5/14 | FR Baseball | Stamford | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Thu., 5/14 | V Boys Golf | Danbury | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 162 Danbury: 164 | ||
| Thu., 5/14 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | W 11-10 | PU:3:30 RE:7:00 | |
| Thu., 5/14 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 4:30 p.m. | PU:2:30 RE:7:00 | |
| Thu., 5/14 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 3-4 | PU:2:30 RE:5:30 | |
| Thu., 5/14 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | JV Travels with Varsity | |
| Thu., 5/14 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Trumbull:197 Ludlowe: 202 | PU:2:20 RE:5:45 | |
| Thu., 5/14 | JV Girls Golf | Trumbull | Away [Directions] | 3:30 p.m. | JV Travels with Varsity | |
| Thu., 5/14 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | L 5-15 | PU:2:30 RE:7:30 | |
| Thu., 5/14 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Thu., 5/14 | V Softball | Stamford | Home - Sturges Park [Directions] | L 3-5 | ||
| Thu., 5/14 | JV Softball | Stamford | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Thu., 5/14 | V Girls Tennis | Greenwich | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/14 | JV Girls Tennis | Greenwich | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | FR Boys Lacrosse | Fairfield Warde | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Fri., 5/15 | FR Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | Cancelled | PU:2:30 RE:5:30 | |
| Sat., 5/16 | V Co-ed Sailing | Silver Cup | Away | 9:00 a.m. | TBA | |
| Mon., 5/18 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | L 3-4 | PU:2:30 RE:6:00 | |
| Mon., 5/18 | JV Baseball | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Mon., 5/18 | FR Baseball | Westhill | Home - Kiwanis Field [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | PU:2:30 RE:5:30 | |
| Mon., 5/18 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:15 p.m. | ||
| Mon., 5/18 | V Girls Golf | Darien | Home - Smith Richardson Golf Course [Directions] | Darien: 205 Ludlowe: 225 | ||
| Mon., 5/18 | JV Girls Golf | Danbury | Home [Directions] | 3:30 p.m. | ||
| Mon., 5/18 | V Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | W 19-6 | PU:2:30 RE:6:30 | |
| Mon., 5/18 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | JV Travels with Varsity | |
| Mon., 5/18 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | Cancelled | PU:4:15 RE:6:30 | |
| Mon., 5/18 | V Girls Outdoor Track | Wilton, Westhill | Away - Allen's Field [Directions] | 4:00 p.m. | PU:2:20 RE:6:00 | 2 Buses |
| Mon., 5/18 | V Softball | Westhill | Home - Sturges Park [Directions] | L 0-5 | ||
| Mon., 5/18 | JV Softball | Westhill | Home - Tom Haydon Field [Directions] | 4:00 p.m. | ||
| Mon., 5/18 | V Girls Tennis | Bridgeport Central | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/18 | JV Girls Tennis | Ridgefield | Home - Tomlinson MS Tennis Courts [Directions] | 4:15 p.m. | ||
| Tue., 5/19 | V Boys Golf | Norwalk | Home - Smith Richardson Golf Course [Directions] | Ludlowe: 159 Norwalk: 193 | ||
| Tue., 5/19 | V Boys Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | W 13-7 | PU:2:30 RE:5:30 | |
| Tue., 5/19 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 6:30 p.m. | PU:4:00 RE:6:45 | |
| Tue., 5/19 | FR Boys Lacrosse | Staples | Home - Sturges Park [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | V Boys Outdoor Track | Westhill, Wilton | Home - Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | JV Girls Tennis | Darien | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | JV Girls Tennis | Darien | Home - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/20 | V Baseball | Wilton | Home - Kiwanis Field [Directions] | L 6-11 | ||
| Wed., 5/20 | JV Baseball | Wilton | Home - Tunxis Hill Park [Directions] | 4:30 p.m. | ||
| Wed., 5/20 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Wed., 5/20 | JV Boys Golf | Darien, Fairfield Warde | Away [Directions] | 3:30 p.m. | PU:2:20 RE:5:45 | |
| Wed., 5/20 | V Boys Lacrosse | Brookfield | Home - Taft Field [Directions] | W 18-6 | ||
| Wed., 5/20 | JV Boys Lacrosse | Brookfield | Home - Taft Field [Directions] | 5:00 p.m. | ||
| Wed., 5/20 | V Girls Golf | Staples | Home - Smith Richardson Golf Course [Directions] | Staples: 183 Ludlowe: 235 | ||
| Wed., 5/20 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | L 1-2 | PU:2:30 RE:5:30 | |
| Wed., 5/20 | JV Softball | Wilton | Away - JV Softball Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Wed., 5/20 | V Girls Tennis | Trumbull | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | FCIAC Quarterfinals | |
| Thu., 5/21 | V Baseball | Danbury | Home - Kiwanis Field [Directions] | L 5-6 | ||
| Thu., 5/21 | JV Baseball | Danbury | Home - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Thu., 5/21 | FR Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Thu., 5/21 | V Boys Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 4-0 | FCIAC Quarterfinals | |
| Thu., 5/21 | V Girls Lacrosse | Guilford | Home - Taft Field [Directions] | W 16-2 | Non League | |
| Thu., 5/21 | JV Girls Lacrosse | Guilford | Home - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 5/21 | V Softball | Danbury | Away - Danbury High School Varsity Softball Field [Directions] | W 2-0 | PU:2:30 RE:5:30 | |
| Thu., 5/21 | JV Softball | Danbury | Away - Danbury High School Junior Varsity Softball Field [Directions] | 4:00 p.m. | JV Travels with Varsity | |
| Fri., 5/22 | V Boys Lacrosse | Ridgefield | Away [Directions] | L 3-15 | PU: 3:15 RE:7:00 | FCIAC Quarterfinals |
| Fri., 5/22 | V Girls Lacrosse | Greenwich | Away [Directions] | L 11-20 | PU:3:45 RE:7:30 | FCIAC Quarterfinals |
| Fri., 5/22 | V Girls Tennis | Wilton | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 4-3 | FCIAC Semi-Finals | |
| Tue., 5/26 | JV Boys Golf | Fairfield Prep | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | No Bus | |
| Tue., 5/26 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS Track | 2:00 p.m. | PU:12:00 RE:8:00 | |
| Tue., 5/26 | V Boys Tennis | Staples | Away [Directions] | 4:00 p.m. | PU:2:30 RE:5:30 | |
| Tue., 5/26 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | Danbury: 179 Ludlowe: 209 | PU:1:55 RE:5:30 | |
| Tue., 5/26 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS Track | 2:00 p.m. | PU:12:00 RE:8:00 | |
| Wed., 5/27 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | New Canaan: 160 Ludlowe: 172 | PU:2:10 RE:5:15 | |
| Mon., 6/1 | V Boys Outdoor Track | CIAC L Championships | Away - Middletown High School | 2:00 p.m. | PU:12:15 RE:8:30 | |
| Mon., 6/1 | V Girls Lacrosse | Greenwich | Home - Taft Field [Directions] | L 8-12 | CIAC First Round | |
| Tue., 6/2 | V Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Warde: 158 Ludlowe: 160 | ||
| Tue., 6/2 | V Girls Outdoor Track | CIAC LL Championship | Away - Willowbrook Park | 2:00 p.m. | PU:12:00 RE:8:30 | |
| Wed., 6/3 | V Boys Golf | FCIAC Championship | Away - Fairchild Wheeler | 12:00 p.m. | ||
| Wed., 6/3 | V Boys Lacrosse | Staples | Home - Taft Field [Directions] | L 4-6 | CIAC First Round | |
| Wed., 6/3 | V Softball | Newington | Away - Softball Field - Behind NHS past Tennis Courts [Directions] | L 2-3 | PU:1:55 RE:5:30 | |
| Wed., 6/3 | V Girls Tennis | Newtown | Home - Fairfield Ludlowe Tennis Courts [Directions] | 12:00 p.m. | Winner plays winner of Greenwich/Bristol Central at Ludlowe at 3:00 | |
| Wed., 6/3 | V Girls Tennis | Greenwich | Home - Fairfield Ludlowe Tennis Courts [Directions] | W 5-2 | State Quarterfinals | |
| Thu., 6/4 | V Girls Tennis | Darien | Home - Fairfield Ludlowe Tennis Courts [Directions] | 3:00 p.m. | State Semi-Finals | |
| Mon., 6/8 | V Boys Golf | State Championships | Away - Timberlin CC | 8:00 a.m. | ||
| Mon., 6/8 | V Boys Outdoor Track | State Open Track Meet | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/8 | V Girls Outdoor Track | State Open Track Meet | Away - Willow Brook Park | 1:30 p.m. | ||