| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/27 | 3:30 PM | Varsity | Scrimmage | Normal | Home | Shelton | | | | Fairfield Ludlowe High School - Main Gym | |
| WED 9/4 | 4:30 PM | Varsity | Non-League | Normal | Home | Conard | Win | 3-2 | | Fairfield Ludlowe High School - Main Gym | |
| MON 9/9 | 5:30 PM | Varsity | Non-League | Normal | Away | Joel Barlow | Loss | 0-3 | | Joel Barlow High School - Lower Gym | 2:30 PM - JV and varsity travel together |
| FRI 9/13 | 6:00 PM | Varsity | Non-League | Normal | Away | Newtown | Win | 3-0 | | Newtown High School - Gym | 3:00 PM - JV and varsity travel together |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | Loss | 0-3 | | Greenwich High School - Gymnasium | 2:30 PM - JV and Varsity travel together |
| THU 9/19 | 4:30 PM | Varsity | League | Normal | Home | Danbury | | | | Fairfield Ludlowe High School - Main Gym | |
| SAT 9/21 | 11:00 AM | Varsity | League | Normal | Away | New Canaan | | | | New Canaan HS - Main Gym | 8:00 AM - JV and Varsity travel together |
| TUE 9/24 | 6:00 PM | Varsity | League | Normal | Away | Westhill | | | | Westhill High School - Main Gym | 3:00 PM - JV and Varsity travel together |
| THU 9/26 | 4:00 PM | Varsity | League | Normal | Away | Brien McMahon | | | | Brien McMahon High School - Kehoe - King Gymnasium | 2:30 PM - JV and Varsity travel together |
| SAT 9/28 | 10:00 AM | Varsity | League | Normal | Home | Norwalk | | | | Fairfield Ludlowe High School - Main Gym | |
| MON 9/30 | 4:30 PM | Varsity | League | Normal | Home | St. Joseph | | | | Fairfield Ludlowe High School - Main Gym | |
| SAT 10/5 | 3:00 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Fairfield University - Leo D. Mahoney Arena | |
| MON 10/7 | 4:30 PM | Varsity | League | Normal | Home | Ridgefield | | | | Fairfield Ludlowe High School - Main Gym | |
| WED 10/9 | 4:00 PM | Varsity | League | Normal | Away | Staples | | | | Staples High School - Staples Gym | 2:45 PM - JV and Varsity travel together |
| THU 10/10 | 4:30 PM | Varsity | Non-League | Normal | Home | Lauralton Hall | | | | Fairfield Ludlowe High School - Main Gym | |
| MON 10/14 | 4:30 PM | Varsity | League | Normal | Home | Stamford | | | | Fairfield Ludlowe High School - Main Gym | |
| WED 10/16 | 4:00 PM | Varsity | League | Normal | Away | Darien | | | | Darien High School - DHS Main Gym | 2:30 PM - JV and Varsity travel together |
| FRI 10/18 | 4:30 PM | Varsity | League | Normal | Home | Wilton | | | | Fairfield Ludlowe High School - Main Gym | |
| MON 10/21 | 4:30 PM | Varsity | League | Normal | Home | Trumbull | | | | Fairfield Ludlowe High School - Main Gym | |
| WED 10/23 | 4:30 PM | Varsity | League | Normal | Home | Bridgeport Central | | | | Fairfield Ludlowe High School - Main Gym | |