| Date | Time | Type | Home School | Away School | Site |
| TUE 3/26 | 4:15 PM | Scrimmage | | Greenwich | Sacred Heart of Greenwich |
| WED 3/27 | 3:45 PM | Scrimmage | Conard | Newington | Conard High School - Tennis Courts |
| WED 3/27 | 4:00 PM | Scrimmage | Wilton | Weston | Wilton Middlebrook School - JV Tennis Courts |
| MON 4/1 | 4:00 PM | League | Fairfield Ludlowe | Darien | Dwight Elementary School - Tennis Courts |
| MON 4/1 | Canceled | Scrimmage | Greenwich | | Binney Park - Binney Park |
| WED 4/3 | Canceled | Non-League | Fairfield Warde | Greenwich | Fairfield Warde High School - Knapps Courts |
| WED 4/3 | Postponed | League | Conard | Newington | Conard High School - Tennis Courts |
| THU 4/4 | 4:00 PM | League | Fairfield Warde | New Canaan | Fairfield Woods - Tennis Courts |
| SAT 4/6 | 12:00 PM | Non-League | Maloney | Rocky Hill | Maloney High School - Tennis Courts |
| MON 4/8 | 4:00 PM | League | Wilton | Fairfield Warde | Wilton Middlebrook School - JV Tennis Courts |
| MON 4/8 | 5:00 PM | League | Greenwich | New Canaan | Binney Park - Binney Park |
| MON 4/8 | 5:00 PM | League | Ridgefield | Staples | Yanity Tennis Courts - Yanity Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Fairfield Warde | St. Joseph | Fairfield Woods - Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Staples | New Canaan | Staples High School - Town Farms Tennis Courts |
| TUE 4/9 | 4:00 PM | League | Ridgefield | Trumbull | Yanity Tennis Courts - Yanity Tennis Courts |
| TUE 4/9 | 4:15 PM | League | Greenwich | Fairfield Ludlowe | Binney Park - Binney Park |
| WED 4/10 | 4:00 PM | League | Trumbull | St. Joseph | Tashua Knolls Golf Course - Tennis Courts |
| WED 4/10 | 4:15 PM | League | | Wilton | Greenwich Academy - Everett Field |
| THU 4/11 | Postponed | League | Fairfield Ludlowe | New Canaan | Dwight Elementary School - Tennis Courts |
| FRI 4/12 | Postponed | League | Greenwich | St. Joseph | Binney Park - Binney Park |
| MON 4/15 | 3:45 PM | Non-League | E.O. Smith | Wethersfield | E.O. Smith High School - Tennis Courts |
| MON 4/15 | 6:00 PM | League | Naugatuck | Ansonia | Naugatuck High School - Tennis Courts |
| MON 4/15 | Postponed | League | Fairfield Ludlowe | New Canaan | Dwight Elementary School - Tennis Courts |
| MON 4/15 | Postponed | League | Ridgefield | St. Joseph | Yanity Tennis Courts - Yanity Tennis Courts |
| TUE 4/16 | 5:00 PM | League | Conard | Maloney | Conard High School - Tennis Courts |
| TUE 4/16 | Postponed | League | Darien | St. Joseph | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| TUE 4/16 | Postponed | League | Wilton | Trumbull | Wilton Middlebrook School - JV Tennis Courts |
| WED 4/17 | 3:45 PM | League | Conard | Rocky Hill | Conard High School - Tennis Courts |
| WED 4/17 | 4:30 PM | League | Hall | Avon | Hall High School - Tennis Courts |
| THU 4/18 | Postponed | League | Avon | Newington | Avon/Thompson Brook School - Avon/Thompson Brook School |
| SAT 4/20 | 10:00 AM | League | Newington | Maloney | Newington High School - Tennis Courts |
| MON 4/22 | 3:45 PM | League | Hall | Conard | Hall High School - Tennis Courts |
| MON 4/22 | 4:00 PM | League | Wilton | New Canaan | Wilton Middlebrook School - JV Tennis Courts |
| MON 4/22 | Postponed | League | Greenwich | Staples | Binney Park - Binney Park |
| TUE 4/23 | 4:00 PM | League | Fairfield Ludlowe | St. Joseph | Dwight Elementary School - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Trumbull | Greenwich | Tashua Knolls Golf Course - Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Darien | Fairfield Warde | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| TUE 4/23 | 4:00 PM | League | Wilton | Staples | Wilton Middlebrook School - JV Tennis Courts |
| WED 4/24 | 3:45 PM | Non-League | E.O. Smith | Rocky Hill | E.O. Smith High School - Tennis Courts |
| WED 4/24 | 4:00 PM | League | Trumbull | Darien | Tashua Knolls Golf Course - Tennis Courts |
| THU 4/25 | 4:00 PM | League | Fairfield Warde | Fairfield Ludlowe | Fairfield Woods - Tennis Courts |
| THU 4/25 | 4:00 PM | League | Darien | New Canaan | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| THU 4/25 | 4:00 PM | League | Wilton | Ridgefield | Wilton Middlebrook School - JV Tennis Courts |
| THU 4/25 | 5:30 PM | League | Simsbury | Avon | Simsbury High School - Tennis Courts |
| THU 4/25 | Postponed | League | Hall | Newington | Hall High School - Tennis Courts |
| FRI 4/26 | 2:30 PM | League | Hall | Maloney | Hall High School - Tennis Courts |
| FRI 4/26 | 4:00 PM | League | Darien | Wilton | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| FRI 4/26 | Postponed | Non-League | Weston | Cardinal Kung Academy | Weston High School - WHS Tennis Courts |
| SAT 4/27 | 10:00 AM | League | Rocky Hill | Southington | Rocky Hill High School - tennis courts |
| SAT 4/27 | 12:00 PM | League | Trumbull | St. Joseph | Trumbull High School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Fairfield Ludlowe | Ridgefield | Dwight Elementary School - Tennis Courts |
| MON 4/29 | 4:00 PM | League | Staples | Fairfield Warde | Staples High School - Town Farms Tennis Courts |
| MON 4/29 | 4:00 PM | League | Wilton | New Canaan | Wilton Middlebrook School - JV Tennis Courts |
| MON 4/29 | 4:15 PM | League | Greenwich | Darien | Binney Park - Binney Park |
| TUE 4/30 | 3:30 PM | League | Windsor | Maloney | Windsor High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Hall | Southington | Hall High School - Tennis Courts |
| TUE 4/30 | 3:45 PM | League | Newington | Rocky Hill | Newington High School - Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Fairfield Warde | Darien | Fairfield Woods - Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Staples | Fairfield Ludlowe | Staples High School - Town Farms Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Wilton | Greenwich | Wilton Middlebrook School - JV Tennis Courts |
| TUE 4/30 | 4:00 PM | League | Ridgefield | New Canaan | Yanity Tennis Courts - Yanity Tennis Courts |
| TUE 4/30 | 5:30 PM | League | Simsbury | Avon | Henry James Middle School - Tennis Courts |
| WED 5/1 | 2:00 PM | League | Hall | | Hall High School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Fairfield Ludlowe | Fairfield Warde | Dwight Elementary School - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Trumbull | Staples | Tashua Knolls Golf Course - Tennis Courts |
| THU 5/2 | 4:00 PM | League | Ridgefield | Greenwich | Yanity Tennis Courts - Yanity Tennis Courts |
| THU 5/2 | 5:00 PM | League | Simsbury | Hall | Henry James Middle School - Tennis Courts |
| FRI 5/3 | 3:45 PM | League | Simsbury | Newington | Simsbury High School - Tennis Courts |
| FRI 5/3 | 4:00 PM | League | Darien | St. Joseph | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| SAT 5/4 | 11:30 AM | League | Maloney | Avon | Maloney High School - Tennis Courts |
| MON 5/6 | 3:45 PM | League | E.O. Smith | Southington | E.O. Smith High School - E.O. Smith High School |
| MON 5/6 | 4:00 PM | League | Staples | New Canaan | Staples High School - Town Farms Tennis Courts |
| MON 5/6 | 4:00 PM | League | Darien | Fairfield Ludlowe | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| MON 5/6 | 4:00 PM | League | Wilton | Fairfield Warde | Wilton Middlebrook School - JV Tennis Courts |
| MON 5/6 | 4:15 PM | League | Greenwich | St. Joseph | Western Middle School - Western Middle School |
| MON 5/6 | Canceled | League | Hall | Conard | Hall High School - Tennis Courts |
| TUE 5/7 | 2:00 PM | League | Watertown | Ansonia | Crestbrook Park - Crestbrook Park Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Fairfield Ludlowe | Wilton | Dwight Elementary School - Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Staples | St. Joseph | Staples High School - Town Farms Tennis Courts |
| TUE 5/7 | 4:00 PM | League | Ridgefield | Darien | Yanity Tennis Courts - Yanity Tennis Courts |
| TUE 5/7 | 4:45 PM | League | Bristol Eastern | Conard | Bristol Eastern High School - Tennis Court |
| TUE 5/7 | 5:30 PM | League | New Canaan | Trumbull | New Canaan HS - NCHS Tennis Courts |
| TUE 5/7 | Canceled | League | Hall | Rocky Hill | Hall High School - Tennis Courts |
| WED 5/8 | 3:45 PM | League | Avon | Hall | Avon Middle School - Avon Middle School |
| WED 5/8 | 3:45 PM | League | Newington | Conard | Newington High School - Tennis Courts |
| WED 5/8 | 4:00 PM | League | Trumbull | Ridgefield | Tashua Knolls Golf Course - Tennis Courts |
| WED 5/8 | 4:00 PM | League | Wilton | St. Joseph | Wilton Middlebrook School - JV Tennis Courts |
| THU 5/9 | 3:45 PM | League | E.O. Smith | South Windsor | E.O. Smith High School - E.O. Smith High School |
| THU 5/9 | 4:00 PM | League | Fairfield Ludlowe | Trumbull | Dwight Elementary School - Tennis Courts |
| THU 5/9 | 4:00 PM | League | Ridgefield | New Canaan | Yanity Tennis Courts - Yanity Tennis Courts |
| THU 5/9 | 4:15 PM | League | Greenwich | Fairfield Warde | Western Middle School - Western Middle School |
| THU 5/9 | 4:30 PM | League | Staples | Wilton | Staples High School - Town Farms Tennis Courts |
| FRI 5/10 | Canceled | League | Greenwich | New Canaan | Binney Park - Binney Park |
| SAT 5/11 | 10:00 AM | League | Southington | Maloney | Southington High School - Tennis Courts |
| SAT 5/11 | Canceled | League | Southington | | Southington High School - Tennis Courts |
| MON 5/13 | 4:00 PM | League | Staples | Darien | Staples High School - Town Farms Tennis Courts |
| MON 5/13 | 4:00 PM | League | Ridgefield | Fairfield Warde | Yanity Tennis Courts - Yanity Tennis Courts |
| MON 5/13 | 4:15 PM | League | Wilton | Greenwich | Wilton Middlebrook School - JV Tennis Courts |
| MON 5/13 | Canceled | League | Hall | E.O. Smith | Hall High School - Tennis Courts |
| TUE 5/14 | 3:45 PM | League | Conard | Rocky Hill | Conard High School - Tennis Courts |
| TUE 5/14 | 4:00 PM | League | Staples | Ridgefield | Staples High School - Town Farms Tennis Courts |
| TUE 5/14 | 4:00 PM | League | Darien | Greenwich | Weed Beach Tennis Courts - Weed Beach Tennis Courts |
| TUE 5/14 | 4:30 PM | League | Fairfield Warde | Trumbull | Fairfield Woods - Tennis Courts |
| TUE 5/14 | 4:30 PM | League | Simsbury | Hall | Simsbury High School - Tennis Courts |
| THU 5/16 | 4:00 PM | League | Wilton | Greenwich | Wilton Middlebrook School - JV Tennis Courts |
| SAT 5/18 | 10:30 AM | League | Southington | Rocky Hill | Southington High School - Tennis Courts |
| SAT 5/18 | 11:00 AM | League | Simsbury | Avon | Simsbury High School - Tennis Courts |
| MON 5/20 | 3:30 PM | League | Newington | Maloney | Newington High School - Tennis Courts |
| MON 5/20 | 5:15 PM | League | Avon | Rocky Hill | Avon Middle School - Avon Middle School |
| WED 5/22 | 2:00 PM | League | Conard | Hall | Conard High School - Tennis Courts |
| WED 5/22 | 3:45 PM | League | Avon | Newington | Avon/Thompson Brook School - Avon/Thompson Brook School |
| FRI 5/24 | Canceled | League | Newington | Rocky Hill | Newington High School - Tennis Courts |