| Date | Time | Type | Home School | Away School | Site |
| FRI 12/12 | 3:30 PM | League | Plumb Hill MS | Indian Mountain School | Connecticut Junior Republic - Pool |
| MON 12/15 | 3:45 PM | League | Plumb Hill MS | Shepaug Valley MS | Connecticut Junior Republic - Pool |
| THU 12/18 | 6:00 PM | League | Long River MS | Whisconier MS | Woodland Regional HS - pool |
| THU 12/18 | Postponed | League | North End MS | Plumb Hill MS | North End Middle School - Main Campus |
| THU 12/18 | Postponed | League | Wallace MS-Waterbury | City Hill MS | Wallace Middle School - Wallace Middle School |
| MON 12/22 | 4:30 PM | League | Shepaug Valley MS | Whisconier MS | Shepaug Valley High School - Shepaug Valley Middle & High School Pool |
| THU 1/8 | 3:45 PM | League | North End MS | City Hill MS | North End Middle School - Main Campus |
| THU 1/8 | 3:45 PM | League | West Side MS-Waterbury | Long River MS | West Side Middle School - West Side Middle School |
| THU 1/8 | 4:30 PM | League | Haddam-Killingworth MS | Hamden Hall | Haddam Killingworth High School (HK) - HKHS Pool - no diving |
| THU 1/8 | 4:30 PM | League | Shepaug Valley MS | MS of Plainville | Shepaug Valley High School - Shepaug Valley Middle & High School Pool |
| FRI 1/9 | 3:45 PM | League | Plumb Hill MS | Indian Mountain School | Connecticut Junior Republic - Pool |
| TUE 1/13 | 4:30 PM | League | West Side MS-Waterbury | Plumb Hill MS | West Side Middle School - West Side Middle School |
| WED 1/14 | 4:30 PM | League | City Hill MS | Shepaug Valley MS | Naugatuck High School - Alex "Gimbo" Sullivan Pool |
| THU 1/15 | 3:45 PM | League | North End MS | Long River MS | North End Middle School - Main Campus |
| THU 1/15 | 3:45 PM | League | West Side MS-Waterbury | City Hill MS | West Side Middle School - West Side Middle School |
| THU 1/15 | 4:30 PM | League | MS of Plainville | HMTCA MS | Plainville High School - Pool |
| FRI 1/16 | 4:00 PM | League | Plumb Hill MS | Wallace MS-Waterbury | Connecticut Junior Republic - Pool |
| FRI 1/16 | 4:30 PM | League | Haddam-Killingworth MS | Williams School | Haddam Killingworth High School (HK) - HKHS Pool - no diving |
| TUE 1/20 | 6:00 PM | League | Long River MS | Wallace MS-Waterbury | Woodland Regional HS - pool |
| TUE 1/20 | Canceled | League | North End MS | Plumb Hill MS | North End Middle School - Main Campus |
| WED 1/21 | 4:30 PM | League | Haddam-Killingworth MS | MS of Plainville | Haddam Killingworth High School (HK) - HKHS Pool - no diving |
| THU 1/22 | 4:30 PM | League | Shepaug Valley MS | Whisconier MS, Plumb Hill MS | Shepaug Valley High School - Shepaug Valley Middle & High School Pool |
| THU 1/22 | 5:45 PM | League | Long River MS | City Hill MS | Woodland High School - Pool |
| FRI 1/23 | 4:00 PM | League | North End MS | Indian Mountain School | North End Middle School - Main Campus |
| MON 1/26 | 4:30 PM | League | MS of Plainville | Plumb Hill MS | Plainville High School - Pool |
| WED 1/28 | 4:30 PM | League | Shepaug Valley MS | Long River MS | Shepaug Valley High School - Shepaug Valley Middle & High School Pool |
| THU 1/29 | Canceled | League | North End MS | Plumb Hill MS, Plumb Hill MS | North End Middle School - Main Campus |
| FRI 1/30 | 4:00 PM | League | West Side MS-Waterbury | Indian Mountain School | West Side Middle School - West Side Middle School |
| WED 2/4 | 4:30 PM | League | Shepaug Valley MS | Indian Mountain School | Shepaug Valley High School - Shepaug Valley Middle & High School Pool |