| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 12/19 | 7:00 p.m. | Varsity | League | Normal | Home | Wolcott | Loss | 46-55 | | Crosby HS-CHS - Augelli Court | |
| MON 12/23 | 7:00 p.m. | Varsity | League | Normal | Home | StPaulCatholic | Loss | 44-77 | | Crosby HS-CHS - Augelli Court | |
| FRI 12/27 | 12:00 p.m. | Varsity | League | Normal | Away | Oxford | Loss | 41-56 | | Oxford High School-Main Gym | |
| MON 12/30 | 2:00 p.m. | Varsity | League | Normal | Away | Brookfield | Loss | 32-43 | | Brookfield High School-BHS Big Gym | |
| FRI 1/3 | 7:00 p.m. | Varsity | League | Normal | Away | WaterburyCareer | Loss | 44-48 | | Waterbury Career Academy-Gymnasium | |
| TUE 1/7 | 7:00 p.m. | Varsity | League | Normal | Away | Torrington | Loss | 36-46 | | Torrington High School | |
| FRI 1/10 | 7:00 p.m. | Varsity | League | Normal | Away | SacredHeart | Loss | 38-66 | | Sacred Heart High School-Alumni Hall | |
| MON 1/13 | 7:00 p.m. | Varsity | League | Normal | Home | HolyCross | Loss | 59-72 | | Crosby HS-CHS - Augelli Court | |
| WED 1/15 | 7:00 p.m. | Varsity | League | Normal | Home | JFKennedy | Loss | 45-49 | | Crosby HS-CHS - Augelli Court | |
| FRI 1/17 | 7:00 p.m. | Varsity | League | Normal | Away | Seymour | Loss | 37-55 | | Seymour High School-Gym | |
| WED 1/22 | 7:00 p.m. | Varsity | League | Normal | Away | Wilby | Win | 63-19 | | Wilby High School-Gym | |
| FRI 1/24 | 5:30 p.m. | Varsity | League | Normal | Home | Derby | Win | 51-42 | | Crosby HS-CHS - Augelli Court | |
| MON 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | WFKaynorRVT | Win | 62-18 | | Crosby HS-CHS - Augelli Court | |
| TUE 1/28 | 7:00 p.m. | Varsity | League | Normal | Home | Ansonia | Loss | 48-54 | | Crosby HS-CHS - Augelli Court | |
| FRI 1/31 | 7:00 p.m. | Varsity | League | Normal | Home | SacredHeart | Loss | 43-61 | | Crosby HS-CHS - Augelli Court | |
| TUE 2/4 | 7:00 p.m. | Varsity | League | Normal | Away | HolyCross | Loss | 41-59 | | Holy Cross-Tim McDonald Gymnasium | |
| FRI 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | WaterburyCareer | Win | 56-31 | | Crosby HS-CHS - Augelli Court | |
| TUE 2/11 | 7:00 p.m. | Varsity | League | Normal | Home | Wilby | Win | 69-16 | | Crosby HS-CHS - Augelli Court | |
| THU 2/13 | 7:00 p.m. | Varsity | League | Normal | Away | JFKennedy | Win | 65-39 | | John F. Kennedy High School-Jack Taglia Gymnasium | |
| TUE 2/18 | 6:00 p.m. | Varsity | League | Normal | Away | Watertown | Win | 58-43 | | Watertown High-Robert B Cook Memorial Gym | |