Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| 3:45 p.m. | Varsity | League | Normal | Home | Immaculate | | | | TBA | |
WED 4/3 | 3:45 p.m. | Varsity | League | Normal | Home | Thomaston | Win | 4-1 | | Shepaug Valley High School Courts | |
FRI 4/5 | 3:45 p.m. | Varsity | League | Normal | Home | Gilbert | Win | 5-0 | | Shepaug Valley High School Courts | |
MON 4/8 | 3:45 p.m. | Varsity | League | Normal | Home | Litchfield | Win | 5-0 | | Shepaug Valley High School Courts | |
WED 4/10 | 3:45 p.m. | Varsity | League | Normal | Away | Nonnewaug | Win | 4-1 | | Edgewood Bath and Tennis - Middlebury | |
THU 4/11 | 3:45 p.m. | Varsity | League | Normal | Away | WamogoReg | Win | 5-0 | | Wamogo Tennis Courts | |
MON 4/15 | 12:00 p.m. | Varsity | League | Normal | Home | NorthwesternReg | Win | 3-2 | | Shepaug Valley High School Courts | |
TUE 4/16 | 10:00 a.m. | Varsity | League | Normal | Away | Brookfield | Win | 6-1 | | BHS Tennis Courts | |
MON 4/22 | 3:45 p.m. | Varsity | League | Normal | Away | LewisMills | Loss | 2-3 | | Lewis Mills Tennis Courts | |
WED 4/24 | 3:45 p.m. | Varsity | League | Normal | Home | HousatonicValleyReg | Win | 3-2 | | Shepaug Valley High School Courts | |
THU 4/25 | 3:45 p.m. | Varsity | League | Normal | Away | Thomaston | Win | 3-2 | | Thomaston Center School | |
MON 4/29 | 3:45 p.m. | Varsity | League | Normal | Away | Gilbert | Win | 5-0 | | Gilbert | |
WED 5/1 | 3:45 p.m. | Varsity | League | Normal | Away | Litchfield | Win | 5-0 | | Pinewoods | |
FRI 5/3 | 3:45 p.m. | Varsity | League | Normal | Home | Nonnewaug | Win | 4-1 | | Shepaug Valley High School Courts | |
MON 5/6 | 3:45 p.m. | Varsity | League | Normal | Home | WamogoReg | Win | 3-2 | | Shepaug Valley High School Courts | |
FRI 5/10 | 4:00 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 5-2 | | Shepaug Valley High School Courts | |
MON 5/13 | 3:45 p.m. | Varsity | League | Normal | Home | LewisMills | Loss | 3-2 | | Shepaug Valley High School Courts | |
THU 5/16 | 3:45 p.m. | Varsity | League | Normal | Away | NorthwesternReg | Win | 4-1 | | Northwestern HS | |
TUE 5/21 | 3:45 p.m. | Varsity | League | Normal | Away | HousatonicValleyReg | Loss | 1-3 | | High School Courts | |
WED 5/22 | 3:45 p.m. | Varsity | League | Normal | Away | HenryAbbottRVT | Win | 4-3 | | Abbott Technical HS Tennis Complex | |