| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 8/31 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Shelton | | | | Shelton High School - Murray Gymnasium | 2:30 PM |
| WED 9/6 | 5:30 PM | Varsity | Scrimmage | Normal | Away | Weston | | | | Weston High School - Gym (New) | 4:00 PM |
| MON 9/11 | 4:00 PM | Varsity | Non-League | Normal | Home | Joel Barlow | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| WED 9/13 | 5:30 PM | Varsity | Non-League | Normal | Away | Conard | Loss | 0-3 | | Conard High School - Main Gym | 2:30 PM |
| THU 9/21 | 4:00 PM | Varsity | Non-League | Normal | Home | Newtown | Loss | 1-3 | | Fairfield Ludlowe High School - Main Gym | |
| FRI 9/22 | 5:30 PM | Varsity | League | Normal | Away | Bridgeport Central | Win | 3-1 | | Bridgeport Central - Barry McLeod Court | 2:30 PM - JV and varsity travel together
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| TUE 9/26 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 3-1 | | Fairfield Ludlowe High School - Main Gym | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| FRI 9/29 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Win | 3-0 | | Danbury High School - Main Gym | 2:30 PM - JV and varsity travel together |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Home | New Canaan | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| THU 10/5 | 4:30 PM | Varsity | League | Normal | Home | Westhill | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| SAT 10/7 | 2:30 PM | Varsity | Non-League | Normal | Home | RHAM | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| MON 10/9 | 4:00 PM | Varsity | League | Normal | Away | Norwalk | Win | 3-0 | | Norwalk High School - Tom Scarso Gymnasium | 2:30 PM - JV and varsity travel together |
| TUE 10/10 | 6:00 PM | Varsity | League | Normal | Home | Fairfield Warde | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| WED 10/11 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Loss | 0-3 | | St. Joseph High School - Gym | 2:30 PM - JV and varsity travel together |
| MON 10/16 | 5:30 PM | Varsity | League | Normal | Away | Ridgefield | Loss | 0-3 | | Ridgefield High School - Main Gym | 2:30 PM - JV and varsity travel together
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| WED 10/18 | 5:30 PM | Varsity | League | Normal | Home | Staples | Loss | 2-3 | | Fairfield Ludlowe High School - Main Gym | |
| FRI 10/20 | 5:30 PM | Varsity | League | Normal | Away | Stamford | Win | 3-2 | | Stamford High School - Kuczo Gymnasium | 2:30 PM - JV and varsity travel together |
| MON 10/23 | 4:00 PM | Varsity | League | Normal | Home | Darien | Loss | 0-3 | | Fairfield Ludlowe High School - Main Gym | |
| WED 10/25 | 5:45 PM | Varsity | League | Normal | Away | Wilton | Win | 3-2 | | Wilton High School - Nicholas Zeoli Field House | 3:00 PM |
| FRI 10/27 | 5:30 PM | Varsity | League | Normal | Away | Trumbull | Loss | 0-3 | | Trumbull High School - THS Main Gym | 2:30 PM - JV and varsity travel together
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