| Middletown 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 625 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | Hall, Capital/Achievement, Crosby (Scrim.) | Away - Hall HS-Stadium (Turf Field) [Directions] | 9:00 a.m. | ||
| Wed., 9/1 | JV Boys Soccer | Portland (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | V Football | Bristol Eastern (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | Scrimmage | |
| Thu., 9/2 | V Boys Soccer | Portland (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | 3:00 p.m. | Cancelled | |
| Thu., 9/2 | JV Girls Soccer | Rocky Hill (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Fri., 9/3 | V Girls Volleyball | Cromwell (Scrim.) | Home - Middletown HS-Main Gym [Directions] | 3:30 p.m. | Closed Scrimmage (NO SPECTATORS ALLOWED) | |
| Fri., 9/3 | JV Girls Volleyball | Cromwell (Scrim.) | Home - Middletown HS-Main Gym [Directions] | 3:30 p.m. | Closed Scrimmage (NO SPECTATORS ALLOWED) | |
| Sat., 9/4 | V Boys Soccer | Lyman Memorial Boys Soccer Jamboree | Away - Lyman Memorial HS-Soccer Field | 9:00 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Berlin (Scrim.) | Away - Sage Park Berlin-Scalise Field [Directions] | 3:00 p.m. | ||
| Tue., 9/7 | V Girls Soccer | Rocky Hill (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Thu., 9/9 | FR Football | Berlin | Away - Sage Park Berlin-Scalise Field [Directions] | 3:30 p.m. | ||
| Thu., 9/9 | V Boys Soccer | Bristol Central | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 9/9 | JV Boys Soccer | Bristol Central | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Postponed | ||
| Thu., 9/9 | V Girls Soccer | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 6:30 p.m. | L 0-2 | |
| Thu., 9/9 | JV Girls Soccer | Bristol Central | Away - Bristol Central HS-Upper Baseball/Soccer Field [Directions] | Postponed | ||
| Fri., 9/10 | V Boys Cross Country | Blue Dragon Invitational | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Boys Cross Country | Portland | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Boys Cross Country | Hale Ray | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Football | Berlin | Away - Sage Park - Berlin-Scalise Field -Turf Field Sage Park Stadium [Directions] | 7:00 p.m. | L 0-33 | |
| Fri., 9/10 | V Girls Cross Country | Blue Dragon Invitational | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:45 p.m. | ||
| Sat., 9/11 | JV Football | Berlin | Away - Sage Park - Berlin-Scalise Field -Turf Field Sage Park Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Girls Soccer | Ellington | Away - Ellington HS-Soccer Field [Directions] | 12:00 p.m. | L 1-5 | |
| Sat., 9/11 | JV Girls Soccer | Ellington | Away - Ellington HS-Soccer Field [Directions] | 2:00 p.m. | ||
| Sat., 9/11 | V Girls Volleyball | CIAC Early Season Tournament | Away - Connecticut Sports Center | 8:00 a.m. | ||
| Mon., 9/13 | V Boys Soccer | Platt | Away - Platt HS-Platt Turf field [Directions] | 3:45 p.m. | W 6-0 | |
| Mon., 9/13 | JV Boys Soccer | Platt | Away - Platt HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 9/13 | V Girls Soccer | Platt | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 9/13 | JV Girls Soccer | Platt | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Canceled | Cancelled | |
| Mon., 9/13 | V Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Johnson Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/13 | JV Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Johnson Gym [Directions] | 5:00 p.m. | ||
| Mon., 9/13 | FR Girls Volleyball | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Stosuy Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | Wethersfield | Away - Wethersfield HS-Backman Pool [Directions] | 5:00 p.m. | 82-94 | |
| Thu., 9/16 | FR Football | Platt | Home - Beman MS-Football Field [Directions] | 3:45 p.m. | ||
| Thu., 9/16 | V Girls Soccer | East Hartford | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 4-2 | |
| Thu., 9/16 | JV Girls Soccer | East Hartford | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Fri., 9/17 | V Football | Platt | Home - Middletown HS-MHS Stadium [Directions] | 7:00 p.m. | L 7-43 | |
| Fri., 9/17 | V Boys Soccer | Windsor | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | W 5-0 | |
| Fri., 9/17 | JV Boys Soccer | Windsor | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/17 | V Girls Swimming and Diving | Farmington | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 84-96 | |
| Fri., 9/17 | V Girls Volleyball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 7:00 p.m. | L 3-0 | |
| Fri., 9/17 | JV Girls Volleyball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 9/17 | FR Girls Volleyball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 9/18 | JV Football | Platt | Home - Middletown HS-MHS Stadium [Directions] | 10:00 a.m. | ||
| Mon., 9/20 | V Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/20 | JV Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 9/20 | FR Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Bristol Central, Plainville | Away - Rockwell Park-Cross Country Course [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Boys Soccer | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 6:00 p.m. | W 4-1 | |
| Tue., 9/21 | JV Boys Soccer | Rocky Hill | Away - Rocky Hill HS-Auxiliary 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Cross Country | Bristol Central, Plainville | Away - Rockwell Park-Cross Country Course [Directions] | 3:45 p.m. | Middletown 15 Bristol Central 46 Middletown 27 Plainville 28 | |
| Tue., 9/21 | V Girls Swimming and Diving | Hall | Home - Middletown HS-MHS Pool [Directions] | 3:30 p.m. | 84-91 | |
| Thu., 9/23 | FR Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 6:30 p.m. | ||
| Thu., 9/23 | V Girls Volleyball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/23 | JV Girls Volleyball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | FR Girls Volleyball | E.O. Smith | Away - E.O. Smith HS-Rear Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | V Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 7:00 p.m. | L 16-20 | |
| Fri., 9/24 | V Boys Soccer | Berlin | Away - Sage Park Berlin-Scalise Field [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 9/24 | V Girls Soccer | Berlin | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 9/24 | JV Girls Soccer | Berlin | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Fri., 9/24 | V Girls Swimming and Diving | Rocky Hill | Home - Middletown HS-MHS Pool [Directions] | 3:45 p.m. | 101-82 | |
| Fri., 9/24 | V Girls Volleyball | Windsor | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | L 3-1 | |
| Fri., 9/24 | JV Girls Volleyball | Windsor | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 9/24 | FR Girls Volleyball | Windsor | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Sat., 9/25 | JV Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | Canceled | Cancelled | |
| Sat., 9/25 | JV Boys Soccer | Berlin | Away - Sage Park Berlin-Scalise Field [Directions] | Postponed | ||
| Mon., 9/27 | V Girls Volleyball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/27 | JV Girls Volleyball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | FR Girls Volleyball | Berlin | Away - Berlin HS-Jim Day Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | Berlin, Maloney | Away - Pistol Creek [Directions] | 3:45 p.m. | ||
| Tue., 9/28 | V Boys Soccer | Plainville | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 9/28 | JV Boys Soccer | Plainville | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | Berlin, Maloney | Away - Pistol Creek [Directions] | 3:45 p.m. | Middletown 25 Maloney 35 Berlin 19 Middletown 36 | |
| Tue., 9/28 | V Girls Soccer | Plainville | Away - Plainville HS-Plainville HS- Tinty Field and Track [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/28 | V Girls Swimming and Diving | Glastonbury | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 81-95 | |
| Wed., 9/29 | V Girls Volleyball | Plainville | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Wed., 9/29 | JV Girls Volleyball | Plainville | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | FR Football | Newington | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Thu., 9/30 | V Girls Soccer | Bloomfield | Away - Bloomfield HS-Phil Rubin Stadium- Turf Field & Track [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 10/1 | V Football | Newington | Home - Middletown HS-MHS Stadium [Directions] | 7:00 p.m. | L 34-56 | gopink night |
| Fri., 10/1 | V Boys Soccer | RHAM | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | T 1-1 | |
| Fri., 10/1 | JV Boys Soccer | RHAM | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 10/1 | V Girls Swimming and Diving | Newington | Home - Middletown HS-MHS Pool [Directions] | 3:30 p.m. | 102-81 | |
| Fri., 10/1 | V Girls Volleyball | East Hartford | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 10/1 | JV Girls Volleyball | East Hartford | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/2 | JV Football | Newington | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/4 | V Boys Soccer | Enfield | Away - Enfield HS-EHS TURF [Directions] | 3:45 p.m. | L 2-1 | |
| Mon., 10/4 | JV Boys Soccer | Enfield | Away - Enfield HS-EHS SOC GRASS 1 [Directions] | Postponed | ||
| Mon., 10/4 | V Girls Volleyball | Lewis Mills | Home - Middletown HS-Main Gym [Directions] | 7:00 p.m. | L 3-1 | |
| Mon., 10/4 | JV Girls Volleyball | Lewis Mills | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Bristol Eastern, Platt | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:45 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Bristol Eastern, Platt | Home - Veterans Memorial Park, Middletown, CT [Directions] | 3:45 p.m. | Middletown 19 Bristol Eastern 42 Middletown 15 Platt 50 | |
| Tue., 10/5 | V Girls Swimming and Diving | Maloney/Platt | Away - Maloney HS-Pool [Directions] | 3:45 p.m. | 95-90 | |
| Wed., 10/6 | V Girls Volleyball | Bulkeley | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Wed., 10/6 | JV Girls Volleyball | Bulkeley | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | FR Football | Southington | Home - Beman MS-Football Field [Directions] | 3:45 p.m. | ||
| Thu., 10/7 | V Boys Soccer | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 10/7 | JV Boys Soccer | Lewis Mills | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Thu., 10/7 | V Girls Soccer | Hartford Public | Away - Hartford Public HS-Soccer Field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/8 | V Football | Southington | Home - Middletown HS-MHS Stadium [Directions] | 6:30 p.m. | L 0-42 | |
| Sat., 10/9 | JV Football | Southington | Home - Middletown HS-MHS Stadium [Directions] | 10:00 a.m. | ||
| Tue., 10/12 | V Boys Cross Country | Lewis Mills | Away - Lewis Mills HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Neil J. Brewer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/12 | JV Boys Soccer | Northwest Catholic | Away - Northwest Catholic HS (Primary)-NWC JV Soccer Field / Track [Directions] | 3:45 p.m. | ||
| Tue., 10/12 | V Girls Cross Country | Lewis Mills | Away - Lewis Mills HS-Cross Country Course [Directions] | 3:45 p.m. | Middletown 23 Lewis Mills 34 | |
| Tue., 10/12 | V Girls Soccer | Manchester | Away - Memorial Field @ MHS [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/12 | JV Girls Soccer | Manchester | Away - Manchester HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/12 | V Girls Swimming and Diving | Bristol Eastern | Away - Dennis Malone Aquatic Center-Dan Malone Aquatic Center [Directions] | 3:45 p.m. | 90-85 | |
| Wed., 10/13 | V Girls Volleyball | Manchester | Away - Manchester HS-Gym [Directions] | 4:30 p.m. | L 3-1 | |
| Wed., 10/13 | JV Girls Volleyball | Manchester | Away - Manchester HS-Gym [Directions] | 3:15 p.m. | ||
| Wed., 10/13 | FR Girls Volleyball | Manchester | Away - Manchester HS-Gym [Directions] | 3:15 p.m. | ||
| Thu., 10/14 | V Boys Soccer | New Britain | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | W 8-0 | |
| Thu., 10/14 | JV Boys Soccer | New Britain | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | V Girls Soccer | Plainville | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | T 1-1 | Go Pink NIght |
| Fri., 10/15 | JV Girls Soccer | Plainville | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/15 | V Girls Swimming and Diving | Bristol Central/Eastern | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 98-82 | Senior Day |
| Fri., 10/15 | V Girls Volleyball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 5:30 p.m. | L 3-0 | Dig Pink |
| Fri., 10/15 | JV Girls Volleyball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/15 | FR Girls Volleyball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/18 | V Girls Volleyball | Platt | Away - Platt HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/18 | JV Girls Volleyball | Platt | Away - Platt HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 10/18 | FR Girls Volleyball | Platt | Away - Platt HS-Gym [Directions] | 3:45 p.m. | ||
| Tue., 10/19 | V Boys Cross Country | CCC XC Championships | Away - Wickham Park | 3:00 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Bristol Eastern | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | W 1-0 | |
| Tue., 10/19 | JV Boys Soccer | Bristol Eastern | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Canceled | Cancelled | |
| Tue., 10/19 | V Girls Cross Country | CCC XC Championships | Away - Wickham Park | 3:00 p.m. | ||
| Tue., 10/19 | V Girls Soccer | Bristol Eastern | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 6:00 p.m. | L 0-4 | |
| Tue., 10/19 | JV Girls Soccer | Bristol Eastern | Away - Bristol Eastern HS-Front Field [Directions] | 3:45 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | Bloomfield | Home - Middletown HS-Main Gym [Directions] | 5:00 p.m. | W 0-3 | Senior Night |
| Wed., 10/20 | JV Girls Volleyball | Bloomfield | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | FR Football | New Britain | Away - Veteran's Stadium-Willow Brook Park-Football Field [Directions] | 3:45 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/21 | JV Girls Volleyball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 10/22 | V Football | New Britain | Away - Veteran's Stadium-Willow Brook Park-Football Field [Directions] | 6:30 p.m. | W 25-6 | |
| Fri., 10/22 | V Boys Soccer | Maloney | Away - Maloney HS-Turf Field [Directions] | 3:45 p.m. | W 4-3 | |
| Fri., 10/22 | JV Boys Soccer | Maloney | Away - Maloney HS-Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Girls Soccer | Maloney | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | L 0-3 | |
| Fri., 10/22 | JV Girls Soccer | Maloney | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Girls Swimming and Diving | Windsor | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 84-98 | Go Pink Event |
| Sat., 10/23 | JV Football | New Britain | Away - Veteran's Stadium-Willow Brook Park-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 10/25 | V Boys Soccer | Rocky Hill | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | W 4-1 | Senior Night |
| Mon., 10/25 | JV Boys Soccer | Rocky Hill | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | Senior Night | |
| Mon., 10/25 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 5:00 p.m. | L 2-3 | |
| Mon., 10/25 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/26 | JV Girls Soccer | Platt | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Canceled | Cancelled | |
| Tue., 10/26 | JV Girls Soccer | Morgan | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Canceled | Cancelled | |
| Tue., 10/26 | V Girls Swimming and Diving | Plainville | Away - Plainville HS-Pool [Directions] | 4:00 p.m. | 76-67 | |
| Wed., 10/27 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:30 p.m. | T 1-1 | |
| Thu., 10/28 | FR Football | Manchester | Away - Memorial Field @ MHS [Directions] | 3:45 p.m. | ||
| Fri., 10/29 | V Football | Manchester | Away - Memorial Field @ MHS [Directions] | 6:00 p.m. | W 37-34 (OT) | |
| Fri., 10/29 | V Boys Soccer | Hartford Public | Away - Hartford Public HS-Soccer Field [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 10/29 | JV Boys Soccer | Hartford Public | Away - Hartford Public HS-JV-Field [Directions] | Canceled | Cancelled | |
| Fri., 10/29 | V Girls Soccer | New Britain | Away - New Britain HS-Veteran's Stadium-Willow Brook Brook Park, New Bri [Directions] | 6:00 p.m. | W 2-0 | |
| Fri., 10/29 | JV Girls Soccer | New Britain | Away - New Britain HS-Willow Brook Soccer fields [Directions] | Canceled | Cancelled | |
| Fri., 10/29 | V Girls Swimming and Diving | Haddam-Killingworth | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 96-82 | |
| Sat., 10/30 | JV Football | Manchester | Away - Memorial Field @ MHS [Directions] | 10:00 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class L Championship | Away - Wickham Park | 11:55 a.m. | ||
| Mon., 11/1 | V Girls Soccer | Platt | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 8-0 | |
| Tue., 11/2 | V Boys Soccer | Lewis Mills | Away - Lewis Mills HS-Nassahegan Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 11/2 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills HS-Soccer JV Field [Directions] | 4:00 p.m. | ||
| Tue., 11/2 | V Girls Soccer | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | L 0-3 | Senior NIght |
| Tue., 11/2 | JV Girls Soccer | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Tue., 11/2 | V Girls Volleyball | Hartford Public | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | W 0-3 | |
| Tue., 11/2 | JV Girls Volleyball | Hartford Public | Home - Middletown HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 11/4 | FR Football | Enfield | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Enfield | Home - Middletown HS-MHS Stadium [Directions] | 6:30 p.m. | W 35-0 | Senior Night |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/5 | V Girls Swimming and Diving | Maloney/Platt, Bristol Central/Eastern, Bristol Eastern, Plainville | Away - Platt HS-Platt Pool [Directions] | 3:30 p.m. | ||
| Sat., 11/6 | JV Football | Enfield | Home - Middletown HS-MHS Stadium [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | L 0-5 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | FR Football | Wethersfield | Away - Samuel B. Webb Elementary School-Webb Field [Directions] | 3:15 p.m. | ||
| Thu., 11/11 | V Boys Soccer | Fitch | Home - Middletown HS-MHS Stadium [Directions] | 2:00 p.m. | L 2-1(OT) | |
| Fri., 11/12 | V Football | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 7:00 p.m. | W 16-13 | |
| Sat., 11/13 | JV Football | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | Canceled | Cancelled | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | FR Football | Windsor | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | Froshmore Game | |
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | Windsor | Home - Middletown HS-MHS Stadium [Directions] | 6:30 p.m. | L 18-33 | |
| Sat., 12/4 | V Boys Ice Hockey | Glastonbury (Scrim.) | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 11:00 a.m. | ||
| Sat., 12/4 | V Girls Basketball | East Hartford (Scrim.) | Home - Middletown HS-Main Gym [Directions] | 9:30 a.m. | Closed Scrimmage - No Spectators/Fans | |
| Tue., 12/7 | V Boys Basketball | Cromwell (Scrim.) | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/7 | V Girls Basketball | Bacon Academy (Scrim.) | Away - Bacon Academy-Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats (Scrim.) | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/11 | V Boys Ice Hockey | Hamden (Scrim.) | Home - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 7:00 p.m. | ||
| Sat., 12/11 | V Wrestling | SCRIMMAGE | Away - Southington HS-Gym West | 9:00 a.m. | ||
| Mon., 12/13 | V Boys Basketball | Capital Prep (Scrim.) | Away - Capital Preparatory Magnet School-Capital Prep [Directions] | 6:00 p.m. | ||
| Tue., 12/14 | V Girls Basketball | Hall | Away - Hall HS-Robinson Gym [Directions] | 6:45 p.m. | W 63-50 | |
| Tue., 12/14 | JV Girls Basketball | Hall | Away - Hall HS-Robinson Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/14 | FR Girls Basketball | Hall | Away - Hall HS-Robinson Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | E.O. Smith-Tolland | Home - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 3:10 p.m. | L 2-3 | |
| Wed., 12/15 | V Wrestling | Wethersfield | Away - Wethersfield HS-Gym A [Directions] | 6:00 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 71-38 | |
| Thu., 12/16 | JV Boys Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 12/17 | V Boys Indoor Track | Hillside Invite | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Fri., 12/17 | V Girls Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | W 60-46 | |
| Fri., 12/17 | JV Girls Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/17 | FR Girls Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 12/17 | V Girls Indoor Track | Hillside Invite | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Sat., 12/18 | V Boys Basketball | East Catholic | Away - Trinity College-Ferris Athletic Center [Directions] | 8:00 p.m. | L 32-70 | |
| Sat., 12/18 | V Boys Ice Hockey | Northeastern Shamrocks | Away - Bolton Ice Palace-Ice Rink [Directions] | 7:00 p.m. | W 7-1 | |
| Sat., 12/18 | V Boys Indoor Track | Hillside Invite | Away - Hillhouse HS-Field House | 9:30 a.m. | ||
| Sat., 12/18 | V Wrestling | Battle at Wethersfield Team Tournament - 4 mats | Away - Wethersfield HS-Gym A | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 12/18 | V Girls Indoor Track | Hillside Invite | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 12/20 | V Boys Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | 6:45 p.m. | W 57-31 | |
| Mon., 12/20 | JV Boys Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/20 | FR Boys Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/20 | V Girls Basketball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 6:45 p.m. | L 52-53 | |
| Mon., 12/20 | JV Girls Basketball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/20 | FR Girls Basketball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 3:45 p.m. | ||
| Tue., 12/21 | V Boys Swimming and Diving | Windsor | Away - Windsor HS-WHS Pool [Directions] | 4:00 p.m. | 83-94 | |
| Wed., 12/22 | V Wrestling | Bristol Eastern | Home - Keigwin MS-Gym 1 [Directions] | 6:00 p.m. | ||
| Thu., 12/23 | V Boys Indoor Track | Hillside Relays | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Thu., 12/23 | V Girls Basketball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 2:00 p.m. | W 59-49 | |
| Thu., 12/23 | JV Girls Basketball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 12:30 p.m. | ||
| Thu., 12/23 | FR Girls Basketball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/23 | V Girls Indoor Track | Hillside Relays | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Mon., 12/27 | V Boys Ice Hockey | SCW Knights | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 7:00 p.m. | W 9-0 | |
| Mon., 12/27 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 6:00 p.m. | W 65-36 | |
| Mon., 12/27 | JV Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 4:15 p.m. | ||
| Wed., 12/29 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks-Rink 2 [Directions] | 12:00 p.m. | L 5-8 | |
| Wed., 12/29 | FR Girls Basketball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | Postponed | ||
| Thu., 12/30 | V Boys Swimming and Diving | Rocky Hill | Away - Rocky Hill HS-Swimming Pool [Directions] | 9:00 a.m. | 90-77 | |
| Thu., 12/30 | V Wrestling | Haddam-Killingworth | Away - Haddam Killingworth MS-Gym 1 [Directions] | Postponed | ||
| Thu., 12/30 | V Girls Basketball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 2:00 p.m. | W 64-37 | |
| Thu., 12/30 | JV Girls Basketball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 12:30 p.m. | ||
| Thu., 12/30 | FR Girls Basketball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 11:00 a.m. | ||
| Thu., 12/30 | V Girls Gymnastics | Valley Regional, H-K/Morgan/Westbrook, TBA, Stonington | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 128.80 | |
| Sun., 1/2 | V Boys Indoor Track | Wilton Wright Invite | Away - SCSU-Gym 1 | 4:00 p.m. | ||
| Sun., 1/2 | V Girls Indoor Track | Wilton Wright Invite | Away - SCSU-Gym 1 | 4:00 p.m. | ||
| Tue., 1/4 | FR Boys Basketball | Platt | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/4 | V Boys Swimming and Diving | Conard | Home - Middletown HS-MHS Pool [Directions] | 5:00 p.m. | 90-95 | |
| Tue., 1/4 | V Girls Basketball | Platt | Away - Platt HS-Gym [Directions] | 5:15 p.m. | W 73-40 | |
| Tue., 1/4 | JV Girls Basketball | Platt | Away - Platt [Directions] | Postponed | ||
| Tue., 1/4 | FR Girls Basketball | Platt | Away - Platt [Directions] | Postponed | ||
| Wed., 1/5 | V Wrestling | Platt | Away - Platt HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/6 | V Wrestling | Haddam-Killingworth, Nonnewaug, Pomperaug Coop | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/7 | JV Girls Basketball | Bloomfield | Away - Bloomfield HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/8 | V Boys Ice Hockey | Hall | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 7:00 p.m. | L 2-4 | |
| Sat., 1/8 | V Boys Indoor Track | Elm City Invite | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 1/8 | V Wrestling | Guilford, Ledyard, Trumbull | Away - Guilford HS-Main gym at GHS [Directions] | 10:00 a.m. | ||
| Sat., 1/8 | V Girls Gymnastics | Foran, H-K/Morgan/Westbrook | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 10:00 a.m. | 117.75 | |
| Sat., 1/8 | V Girls Indoor Track | Elm City Invite | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 1/10 | V Boys Basketball | East Hartford | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | L 61-66 | |
| Mon., 1/10 | JV Boys Basketball | East Hartford | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/10 | FR Boys Basketball | East Hartford | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/11 | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS-Pool [Directions] | 3:45 p.m. | ||
| Tue., 1/11 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield HS-Backman Pool [Directions] | 5:00 p.m. | 85-99 | |
| Tue., 1/11 | V Girls Basketball | Northwest Catholic | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | W 80-65 | |
| Tue., 1/11 | JV Girls Basketball | Northwest Catholic | Home - Middletown HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/11 | FR Girls Basketball | Northwest Catholic | Home - Middletown HS-Main Gym [Directions] | Postponed | ||
| Wed., 1/12 | V Boys Ice Hockey | Conard | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:05 p.m. | W 3-2 | |
| Wed., 1/12 | V Wrestling | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/13 | V Boys Basketball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 6:45 p.m. | W 42-28 | |
| Thu., 1/13 | JV Boys Basketball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Boys Basketball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Berlin | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | L 61-50 | |
| Thu., 1/13 | JV Girls Basketball | Berlin | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Girls Basketball | Berlin | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | V Girls Gymnastics | Daniel Hand, Morgan, TBA, Valley Regional, Westbrook | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | ||
| Fri., 1/14 | V Boys Indoor Track | Hillhouse Varsity Night Meet | Away - Hillhouse HS-Field House | Canceled | Cancelled | |
| Fri., 1/14 | V Boys Swimming and Diving | Farmington | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 86-92 | |
| Fri., 1/14 | V Wrestling | South Windsor | Away - Park and Recreation Building-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Indoor Track | Hillhouse Varsity Night Meet | Away - Hillhouse HS-Field House | Canceled | Cancelled | |
| Sat., 1/15 | V Boys Ice Hockey | SCW Knights | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 12:00 p.m. | W 7-1 | |
| Sat., 1/15 | V Wrestling | RHAM, Bristol Eastern, Plainville | Away - RHAM HS-Gym [Directions] | 10:00 a.m. | ||
| Tue., 1/18 | V Boys Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 6:45 p.m. | L 50-80 | |
| Tue., 1/18 | JV Boys Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 1/18 | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS-Pool [Directions] | 4:00 p.m. | 76-102 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Tue., 1/18 | V Girls Basketball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 66-48 | |
| Tue., 1/18 | JV Girls Basketball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/19 | V Boys Basketball | Prince Tech | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 48-43 | |
| Wed., 1/19 | JV Boys Basketball | Prince Tech | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/19 | FR Boys Basketball | Prince Tech | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:05 p.m. | W 4-3 | |
| Wed., 1/19 | V Wrestling | RHAM | Home - Keigwin MS-Gym 1 [Directions] | 6:00 p.m. | ||
| Thu., 1/20 | V Girls Gymnastics | TBA, Hamden | Away - TBA | 6:00 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 62-49 | |
| Fri., 1/21 | JV Boys Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Manchester | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Bloomfield | Away - Bloomfield HS-Main Gym [Directions] | 3:45 p.m. | W 65-35 | |
| Sat., 1/22 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Storrs-Freitas Ice Forum [Directions] | 7:30 p.m. | L 1-5 | |
| Sat., 1/22 | V Boys Indoor Track | SCC Coaches Invitational | Home - Hillhouse HS-Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/22 | V Wrestling | The 35th Annual New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Valley Regional, H-K/Morgan/Westbrook, Hamden, TBA | Away - Flip Flop Gymnastics [Directions] | TBA | 106.95 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Sat., 1/22 | V Girls Indoor Track | SCC Coaches Invitational | Home - Hillhouse HS-Field House [Directions] | 9:00 a.m. | ||
| Sun., 1/23 | V Boys Ice Hockey | Woodstock Academy | Away - Pomfret School-Jahn Rink [Directions] | 2:30 p.m. | L 0-4 | |
| Mon., 1/24 | V Boys Basketball | Hartford Public | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 57-52 | |
| Mon., 1/24 | JV Boys Basketball | Hartford Public | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/24 | FR Boys Basketball | Hartford Public | Home - Middletown HS-Main Gym [Directions] | Postponed | ||
| Tue., 1/25 | V Boys Swimming and Diving | Berlin | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 97-86 | |
| Tue., 1/25 | V Girls Basketball | Simsbury | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 54-49 | |
| Tue., 1/25 | JV Girls Basketball | Simsbury | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | Wethersfield | Away - Newington Ice Arena-Blue Rink [Directions] | 5:00 p.m. | L 1-4 | |
| Wed., 1/26 | V Wrestling | Plainville | Away - Plainville HS-Kegel Gymansium [Directions] | 6:00 p.m. | ||
| Wed., 1/26 | FR Girls Basketball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/27 | V Boys Basketball | Enfield | Away - Enfield HS-EHS GYM - MAIN [Directions] | 6:45 p.m. | W 61-49 | |
| Thu., 1/27 | JV Boys Basketball | Enfield | Away - Enfield HS-EHS GYM - MAIN [Directions] | 5:15 p.m. | ||
| Thu., 1/27 | FR Boys Basketball | Enfield | Away - Enfield HS-EHS GYM - MAIN [Directions] | 3:45 p.m. | ||
| Fri., 1/28 | V Boys Swimming and Diving | Suffield | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 94-70 | |
| Fri., 1/28 | V Girls Basketball | Conard | Away - Conard HS-Main Gym [Directions] | 6:45 p.m. | W 47-26 | |
| Fri., 1/28 | JV Girls Basketball | Conard | Away - Conard HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/28 | FR Girls Basketball | Conard | Away - Conard HS-Main Gym [Directions] | 3:45 p.m. | ||
| Sat., 1/29 | V Boys Indoor Track | CCC Indoor Track & Field Championships - Boys | Away - E.O. Smith HS-Floyd Little Athletic Center - New Haven, CT | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/6, Time to 5:00 p.m. | ||||||
| Sat., 1/29 | FR Girls Basketball | New Britain | Away - New Britain HS-Gym [Directions] | Postponed | ||
| Sat., 1/29 | V Girls Indoor Track | CCC Indoor Track & Field Championships - Girls | Away - E.O. Smith HS-Floyd Little Athletic Center - New Haven, CT | 9:00 a.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/6, Time to 5:00 p.m. | ||||||
| Mon., 1/31 | V Boys Basketball | Plainville | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 71-33 | |
| Mon., 1/31 | JV Boys Basketball | Plainville | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/31 | FR Boys Basketball | Plainville | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Plainville Boys Swimming | Away - Plainville HS-Pool [Directions] | 4:00 p.m. | 84-53 | |
| Tue., 2/1 | V Girls Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 6:45 p.m. | W 51-22 | |
| Tue., 2/1 | JV Girls Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/2 | V Boys Basketball | Platt | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | W 69-48 | |
| Wed., 2/2 | JV Boys Basketball | Platt | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | Hall | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 2-3 | |
| Thu., 2/3 | V Boys Basketball | Newington | Away - Newington HS-Gym [Directions] | 6:45 p.m. | L 57-65 | |
| Thu., 2/3 | JV Boys Basketball | Newington | Away - Newington HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | FR Boys Basketball | Newington | Away - Newington HS-Gym [Directions] | 3:45 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Wethersfield | Away - Wethersfield HS-Gym A [Directions] | 6:45 p.m. | W 61-32 | |
| Thu., 2/3 | JV Girls Basketball | Wethersfield | Away - Wethersfield HS-Gym A [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | FR Girls Basketball | Wethersfield | Away - Wethersfield HS-Gym A [Directions] | Postponed | ||
| Sat., 2/5 | V Boys Ice Hockey | East Catholic | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 7:00 p.m. | L 3-2 | |
| Sat., 2/5 | V Wrestling | 2022 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy-Gym | 9:00 a.m. | ||
| Mon., 2/7 | V Boys Basketball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 67-51 | Senior Night |
| Mon., 2/7 | JV Boys Basketball | Bristol Eastern | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | FR Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/7 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 3:50 p.m. | L 4-6 | |
| Mon., 2/7 | V Girls Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 6:45 p.m. | W 62-54 | |
| Mon., 2/7 | JV Girls Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | FR Girls Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/8 | V Boys Swimming and Diving | Lewis Mills | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 95-79 | Senior Night |
| Tue., 2/8 | V Girls Basketball | Sheehan | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | W 61-49 | |
| Tue., 2/8 | JV Girls Basketball | Sheehan | Home - Middletown HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/8 | V Girls Gymnastics | Jonathan Law, Oxford | Away - Jonathan Law HS-Old Gym [Directions] | 6:30 p.m. | 119.55 | |
| Wed., 2/9 | V Boys Ice Hockey | Newington Coop | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 4:20 p.m. | L 7-2 | |
| Wed., 2/9 | V Boys Swimming and Diving | Meriden Co-op | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 95-91 | |
| Wed., 2/9 | V Wrestling | Berlin | Home - Keigwin MS-Gym 1 [Directions] | 6:00 p.m. | Senior Night | |
| Wed., 2/9 | V Girls Basketball | Amistad | Home - Middletown HS-Main Gym [Directions] | 5:30 p.m. | W 59-49 | |
| Wed., 2/9 | JV Girls Basketball | Amistad | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/10 | V Boys Basketball | Maloney | Away - Maloney HS [Directions] | 6:45 p.m. | W 58-41 | |
| Thu., 2/10 | JV Boys Basketball | Maloney | Away - Maloney HS [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | FR Boys Basketball | Maloney | Away - Maloney HS [Directions] | 3:45 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | W 67-36 | |
| Thu., 2/10 | JV Girls Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | FR Girls Basketball | Maloney | Home - Middletown HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/10 | V Girls Gymnastics | Jonathan Law, Daniel Hand, Hamden, Foran | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:00 p.m. | 118.65 | |
| Fri., 2/11 | V Boys Basketball | Weaver | Away - Weaver HS-Doc Hurley Fieldhouse [Directions] | 5:45 p.m. | L 59-66 | |
| Sat., 2/12 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Mass Mutual Center-Rink [Directions] | 1:30 p.m. | W Forfeit | |
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 2/12 | V Wrestling | CCC Meet | Away - Simsbury HS-Gym 2 | Canceled | Cancelled | |
| Sat., 2/12 | FR Girls Basketball | New Britain | Away - New Britain HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 2/14 | V Boys Swimming and Diving | Southington | Home - Middletown HS-MHS Pool [Directions] | 4:00 p.m. | 89-92 | |
| Mon., 2/14 | V Girls Basketball | Lewis Mills | Home - Middletown HS-Main Gym [Directions] | 5:30 p.m. | W 64-36 | Senior Night |
| Mon., 2/14 | JV Girls Basketball | Lewis Mills | Home - Middletown HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 6:45 p.m. | L 34-80 | |
| Tue., 2/15 | JV Boys Basketball | Bristol Central | Home - Middletown HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | T 0-0 | |
| Wed., 2/16 | Miscellaneous Events | Art Rich WINTER Sports Team Pictures | Home - Middletown HS-Main Gym [Directions] | 2:20 p.m. | Team Pictures, Coaches will receive schedule | |
| Thu., 2/17 | V Girls Basketball | Conard | Home - Middletown HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Girls Gymnastics | Daniel Hand, H-K/Morgan/Westbrook, Morgan, Valley Regional, Westbrook | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | 120.45 | |
| Fri., 2/18 | V Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | 6:45 p.m. | W 57-39 | |
| Fri., 2/18 | JV Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/18 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Away - HMTCA [Directions] | 3:45 p.m. | ||
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 5:15 p.m. | W 51-47 | |
| Sat., 2/19 | JV Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 2:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | New Milford | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 4:50 p.m. | L 2-3(OT) | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Girls Gymnastics | Valley Regional, H-K/Morgan/Westbrook | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 124.45 | |
| Tue., 2/22 | V Boys Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 6:45 p.m. | W 66-58 | |
| Tue., 2/22 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/22 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 2/22 | V Boys Swimming and Diving | Bristol Eastern | Away - Dennis Malone Aquatic Center-Dan Malone Aquatic Center [Directions] | 5:30 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 3:10 p.m. | L 2-7 | |
| Thu., 2/24 | V Boys Basketball | Farmington | Home - Middletown HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/26 | V Boys Basketball | Bristol Central | Away - Enfield HS-EHS GYM - MAIN [Directions] | 11:00 a.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 8:20 p.m. | L 2-7 | |
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | Winter Dance Team | CIAC State Dance Championship | Away - Hamden HS-HHS Gym | 9:00 a.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Thu., 3/3 | V Boys Basketball | New Britain (Scrim.) | Away - New Britain HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 3/3 | V Girls Basketball | Stamford | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Ice Hockey | East Catholic (Scrim.) | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 3:30 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Mon., 3/7 | V Boys Basketball | Jonathan Law | Home - Middletown HS-Main Gym [Directions] | 5:45 p.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 5:00 p.m. | ||
| Mon., 3/7 | V Girls Basketball | Danbury | Home - Middletown HS-Main Gym [Directions] | 7:45 p.m. | ||
| Thu., 3/10 | V Boys Basketball | Prince Tech | Away - Prince Tech / Mark Snyder Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/11 | V Boys Basketball | Conard | Away - Conard HS-Main Gym [Directions] | 6:30 p.m. | ||
| Fri., 3/11 | V Girls Basketball | East Hartford | Away - New Britain HS-Gym [Directions] | 6:00 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Fri., 3/25 | V Softball | Cromwell (Scrim.) | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:30 p.m. | ||
| Wed., 3/30 | V Baseball | Hillhouse/Career (Scrim.) | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | W 18-3 | |
| Wed., 3/30 | V Girls Lacrosse | Northwest Catholic (Scrim.) | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Thu., 3/31 | V Baseball | New Britain (Scrim.) | Away - Beehive Field-Baseball Diamond [Directions] | 3:45 p.m. | W 5-4 | |
| Fri., 4/1 | JV Ultimate Frisbee | Xavier | Home - Moody School-Lacrosse Field 2 [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | Miscellaneous Events | Alumni Boys Basketball Game | Home - Middletown HS-Main Gym [Directions] | 6:00 p.m. | ||
| Sat., 4/2 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 1:00 p.m. | W 11-2 | |
| Sat., 4/2 | V Boys Lacrosse | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 10:30 a.m. | L 12-2 | |
| Sat., 4/2 | JV Boys Lacrosse | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Canceled | Cancelled | |
| Sat., 4/2 | V Co-ed Crew | Guilford | Away - Guilford HS-Lake Quonnipaug [Directions] | 8:30 a.m. | ||
| Sat., 4/2 | V Softball | Windsor (Scrim.) | Away - Windsor HS-WHS Varsity Softball Field [Directions] | 10:30 a.m. | ||
| Mon., 4/4 | V Girls Lacrosse | Old Lyme | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | L 5-15 | |
| Mon., 4/4 | V Girls Tennis | Tolland | Home - Beman MS-BEMAN Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/5 | V Baseball | Bloomfield | Home - Palmer Field-Baseball Diamond [Directions] | 6:00 p.m. | W 14-0 | |
| Tue., 4/5 | V Boys Outdoor Track | Plainville | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | Plainville 101 Middletown 49 | |
| Tue., 4/5 | V Girls Outdoor Track | Plainville | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | [Detailed Results] | |
| Tue., 4/5 | V Softball | Northwest Catholic | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | W 19-1 | |
| Tue., 4/5 | V Girls Tennis | East Catholic | Home - Beman MS-BEMAN Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/6 | V Boys Lacrosse | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 4:00 p.m. | L 18-3 | |
| Wed., 4/6 | V Ultimate Frisbee | Avon | Away - Avon/Thompson Brook School [Directions] | 4:30 p.m. | ||
| Thu., 4/7 | V Boys Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 5:15 p.m. | L 15-0 | |
| Fri., 4/8 | FR Baseball | Bristol Central | Home - Keigwin MS-Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | JV Softball | Bristol Central | Away - South Side School-Softball Field [Directions] | Canceled | Cancelled | |
| Sat., 4/9 | JV Baseball | Bristol Central | Away - Bristol Central HS-Lower Baseball/Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 4/9 | V Co-ed Crew | Stonington | Away - Stonington HS-Mystic Seaport [Directions] | 2:30 p.m. | ||
| Mon., 4/11 | V Baseball | Platt | Away - Platt HS-Baseball Diamond [Directions] | 3:45 p.m. | L 4-2 | |
| Mon., 4/11 | V Softball | Platt | Home - Pat Kidney Field-Softball field [Directions] | 3:45 p.m. | L 5-1 | |
| Mon., 4/11 | JV Softball | Platt | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | JV Baseball | Platt | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | L 14-6 | |
| Tue., 4/12 | V Boys Outdoor Track | Maloney | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | Middletown 83 Maloney 60 | |
| Tue., 4/12 | V Girls Outdoor Track | Maloney | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | Middletown 95- Maloney 46 | |
| Wed., 4/13 | V Baseball | Plainville | Away - Plainville HS-Varsity Baseball Diamond [Directions] | 3:45 p.m. | W 9-2 | |
| Wed., 4/13 | FR Baseball | Plainville | Away - Plainville HS-JV Baseball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Softball | Rocky Hill | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 6:00 p.m. | L 7-2 | |
| Wed., 4/13 | JV Softball | Rocky Hill | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Thu., 4/14 | V Baseball | Rockville | Away - Rockville HS-Upper Field [Directions] | 3:45 p.m. | W 7-4 | |
| Thu., 4/14 | FR Baseball | Conard | Away - Conard HS-Baseball Diamond [Directions] | 2:30 p.m. | W 12-7 | |
| Thu., 4/14 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 5-0 | |
| Mon., 4/18 | V Baseball | Hall | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | L 4-2 | |
| Mon., 4/18 | FR Baseball | Hall | Home - Keigwin MS-Baseball Field [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 4/18 | V Boys Lacrosse | Windsor | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | W 15-5 | |
| Mon., 4/18 | V Softball | Avon | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | L 10-2 | |
| Mon., 4/18 | V Girls Tennis | Windsor | Away - Windsor HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 4/19 | V Boys Golf | Maloney | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 188 Maloney 208 Medalist: Andrew Dunn | |
| Tue., 4/19 | V Boys Outdoor Track | Bristol Central | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | V Girls Outdoor Track | Bristol Central | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | 66 Middletown - Bristol Central 83 | |
| Wed., 4/20 | JV Baseball | Hall | Away - Hall HS-Varsity Baseball Diamond [Directions] | 3:45 p.m. | L 20-0 | |
| Wed., 4/20 | V Boys Crew | East Lyme | Away - East Lyme HS-Emerson Boat House [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Lacrosse | Vinal-Goodwin | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | W 15-3 | |
| Wed., 4/20 | V Ultimate Frisbee | Choate Rosemary Hall | Home - Moody School-Lacrosse Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | JV Ultimate Frisbee | Choate Rosemary Hall | Home - Moody School-Lacrosse Field 2 [Directions] | 3:30 p.m. | ||
| Wed., 4/20 | V Girls Crew | East Lyme | Away - East Lyme HS-Emerson Boat House [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Girls Lacrosse | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | W 14-2 | |
| Thu., 4/21 | V Boys Golf | Platt | Away - Hunter Golf Club [Directions] | 3:00 p.m. | Middletown 179 Platt 215 Medalist: Andrew Dunn | |
| Thu., 4/21 | V Boys Lacrosse | E.O. Smith | Away - Farrell Field Park-Upper Field [Directions] | 3:45 p.m. | L 15-5 | |
| Thu., 4/21 | JV Boys Lacrosse | E.O. Smith | Away - Farrell Field Park-Upper Field [Directions] | Canceled | Cancelled | |
| Thu., 4/21 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 10-19 | |
| Thu., 4/21 | V Softball | Haddam-Killingworth | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | L 11-2 | |
| Thu., 4/21 | V Girls Tennis | Enfield | Home - Middletown Tennis Courts-Beman Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/23 | V Baseball | Bristol Central | Home - Palmer Field-Baseball Diamond [Directions] | 11:00 a.m. | W 9-2 | |
| Sat., 4/23 | V Boys Lacrosse | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 11:00 a.m. | L 1-16 | |
| Sat., 4/23 | JV Boys Lacrosse | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | Canceled | Cancelled | |
| Sun., 4/24 | V Co-ed Crew | E.O. Smith | Away - Coventry Lake - Patriot's Park [Directions] | TBA | ||
| Mon., 4/25 | V Baseball | Berlin | Away - Sage Park Berlin-Zipadelli Field [Directions] | 3:45 p.m. | L 3-2 (8) | |
| Mon., 4/25 | FR Baseball | Berlin | Away - Percival Park-Baretta Field [Directions] | Postponed | ||
| Mon., 4/25 | V Boys Golf | Bristol Central | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | Middletown 192 Bristol Central 195 | |
| Mon., 4/25 | V Boys Lacrosse | Tolland | Away - Tolland HS-Stadium [Directions] | 4:00 p.m. | L 13-2 | |
| Mon., 4/25 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 4:00 p.m. | W 9-7 | |
| Mon., 4/25 | V Softball | Berlin | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | L 8-2 | |
| Mon., 4/25 | JV Softball | Berlin | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Mon., 4/25 | V Girls Tennis | New Britain | Away - New Britain HS-tennis courts [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/26 | V Boys Golf | Bristol Eastern | Away - Maloney [Directions] | 3:00 p.m. | Middletown 176 Bristol Eastern 217 Medalist: Andrew Dunn | |
| Tue., 4/26 | V Girls Lacrosse | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 5:30 p.m. | L 8-20 | |
| Wed., 4/27 | V Baseball | Plainville | Home - Palmer Field-Baseball Diamond [Directions] | 3:45 p.m. | W 5-4 | |
| Wed., 4/27 | V Ultimate Frisbee | Hotchkiss | Away - Hotchkiss School | 4:45 p.m. | ||
| Wed., 4/27 | JV Ultimate Frisbee | Hotchkiss | Away - Hotchkiss School | 4:45 p.m. | ||
| Wed., 4/27 | V Girls Lacrosse | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 3:30 p.m. | L 8-19 | |
| Wed., 4/27 | V Softball | Plainville | Away - Plainville HS-Varsity Softball Turf Diamond [Directions] | 6:30 p.m. | L 16-5 | |
| Wed., 4/27 | JV Softball | Plainville | Away - Plainville HS-Plainville HS- Varsity Softball Field (Turf) [Directions] | 3:45 p.m. | ||
| Thu., 4/28 | JV Baseball | Plainville | Away - Plainville HS-JV Baseball Diamond [Directions] | 3:45 p.m. | L 3-1 | |
| Thu., 4/28 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:00 p.m. | Middletown 182 Coginchaug 214 Co Medalist: Andrew Dunn | |
| Thu., 4/28 | V Boys Lacrosse | Enfield | Away - Enfield HS-EHS TURF [Directions] | 4:00 p.m. | L 10-5 | |
| Thu., 4/28 | V Girls Tennis | Simsbury | Away - Simsbury HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/29 | V Baseball | Avon | Home - Palmer Field-Baseball Diamond [Directions] | 3:45 p.m. | W 5-4 | |
| Fri., 4/29 | V Girls Lacrosse | Bristol Eastern | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 5:00 p.m. | L 10-13 | |
| Fri., 4/29 | V Softball | Platt | Away - Platt HS-Softball Diamond [Directions] | 3:45 p.m. | L 8-7 | |
| Fri., 4/29 | JV Softball | Platt | Away - Lincoln MS Platt JV [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Girls Tennis | Platt | Away - Platt HS-Tennis Court [Directions] | 3:45 p.m. | W 5-2 | |
| Sat., 4/30 | JV Baseball | Avon | Away - Avon HS-Baseball Diamond [Directions] | 10:00 a.m. | L 11-9 | |
| Sat., 4/30 | V Boys Outdoor Track | Ledyard | Away - Ledyard HS-Ledyard High School Track [Directions] | 9:00 a.m. | ||
| Sat., 4/30 | V Ultimate Frisbee | Middletown Ultimate Invitational | Home - Middletown HS-MHS Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/30 | JV Ultimate Frisbee | Middletown Ultimate Invitational | Home - Middletown HS-MHS Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | Ledyard | Away - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | ||
| Mon., 5/2 | FR Baseball | Tolland | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | W 12-11 | |
| Mon., 5/2 | V Boys Lacrosse | Windsor (Scrim.) | Away - Windsor HS-Jack O'Brien Stadium [Directions] | 6:30 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Bristol Eastern | Away - Bristol Eastern HS-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Lacrosse | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 4:30 p.m. | L 4-8 | |
| Tue., 5/3 | V Girls Outdoor Track | Bristol Eastern | Away - Bristol Eastern HS-Track [Directions] | 3:45 p.m. | 67 Bristol Eastern- Middletown 79 | |
| Tue., 5/3 | V Softball | Bloomfield | Away - Bloomfield HS-Softball Diamond [Directions] | 3:45 p.m. | W 21-0 | |
| Tue., 5/3 | V Girls Tennis | Bristol Central | Away - Bristol Central HS-Tennis Courts [Directions] | 4:15 p.m. | L 1-6 | |
| Wed., 5/4 | V Ultimate Frisbee | North Branford | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Thu., 5/5 | JV Baseball | Bristol Central | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Boys Golf | Bristol Central | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 179 Bristol Central 183 | |
| Thu., 5/5 | V Boys Lacrosse | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 5:30 p.m. | L 16-4 | |
| Thu., 5/5 | V Girls Lacrosse | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 6:30 p.m. | W 15-12 | |
| Thu., 5/5 | V Softball | New Britain | Away - Martha Hart Park, New Britain [Directions] | 3:45 p.m. | L 3-2 | |
| Thu., 5/5 | JV Softball | New Britain | Away - Chesley Park [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Plainville | Home - Middletown Tennis Courts-Beman Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 5/6 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Field #1 - Brookside Field @ CRHS [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Golf | Plainville | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 167 Plainville 224 Medalist: Andrew Dunn 38 | |
| Fri., 5/6 | V Boys Outdoor Track | Wethersfield | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Boys Outdoor Track | Daniel Hand | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Boys Outdoor Track | Cheshire | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | Wethersfield | Home - Middletown HS-MHS Stadium [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | Cheshire | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Cheshire | Home - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Daniel Hand | Home - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Berlin | Home - Berlin HS-Biscoglio Track [Directions] | TBA | ||
| Sat., 5/7 | V Co-ed Crew | Valley Regional | Home - Boathouse [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 5/7 | V Girls Outdoor Track | East Hartford | Home - Middletown HS-MHS Stadium [Directions] | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Daniel Hand | Away - Daniel Hand HS-DHHS Track [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Simsbury | Home - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Cheshire | Home - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Berlin | Home - Middletown HS-MHS Stadium [Directions] | TBA | ||
| Mon., 5/9 | V Baseball | RHAM | Home - Palmer Field-Baseball Diamond [Directions] | 3:45 p.m. | L 3-1 | |
| Mon., 5/9 | FR Baseball | E.O. Smith | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/9 | V Girls Lacrosse | Windsor | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | W 17-12 | |
| Mon., 5/9 | V Softball | Conard | Home - Pat Kidney Field-Softball field [Directions] | 6:00 p.m. | W 4-1 | |
| Mon., 5/9 | JV Softball | Conard | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Southington | Away - Southington HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/10 | V Boys Lacrosse | RHAM | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | L 19-3 | |
| Tue., 5/10 | V Boys Outdoor Track | Platt | Away - Platt HS-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Ultimate Frisbee | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 7:00 p.m. | ||
| Tue., 5/10 | JV Ultimate Frisbee | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | E.O. Smith | Away - Farrell Field Park-Upper Field [Directions] | 3:45 p.m. | L 6-14 | |
| Tue., 5/10 | V Girls Outdoor Track | Platt | Away - Platt HS-Track [Directions] | 3:45 p.m. | 48 Platt - Middletown 98 | |
| Wed., 5/11 | V Baseball | Bristol Eastern | Home - Palmer Field-Baseball Diamond [Directions] | 4:15 p.m. | L 7-4 | |
| Wed., 5/11 | FR Baseball | Bristol Eastern | Home - Middletown HS-MHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/11 | V Girls Lacrosse | Bristol Eastern | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 7:00 p.m. | L 5-17 | |
| Wed., 5/11 | V Softball | Bristol Eastern | Away - Bristol Eastern HS-Softball Field [Directions] | 3:45 p.m. | L 6-2 | |
| Wed., 5/11 | JV Softball | Bristol Eastern | Away - Bristol Eastern HS-Page Park [Directions] | 3:45 p.m. | ||
| Wed., 5/11 | V Girls Tennis | Berlin | Home - Middletown Tennis Courts-Beman Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/12 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | L 5-2 | |
| Thu., 5/12 | JV Baseball | Bristol Eastern | Away - Bristol Eastern HS-Baseball Field #2 [Directions] | Postponed | L 24-9 | |
| Thu., 5/12 | V Boys Golf | Maloney | Away - Hunter Golf Club [Directions] | 3:00 p.m. | Middletown 185 Maloney 198 Medalist: Andrew Dunn 40 | |
| Thu., 5/12 | V Boys Lacrosse | Bristol Coop | Home - Middletown HS-MHS Stadium [Directions] | 5:00 p.m. | L 19-4 | |
| Thu., 5/12 | V Softball | Morgan | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | W 8-0 | |
| Fri., 5/13 | V Baseball | Maloney | Away - Maloney HS-Baseball Diamond [Directions] | 3:45 p.m. | L 9-1 | |
| Fri., 5/13 | V Softball | Maloney | Home - Middletown HS-MHS Softball Field [Directions] | 3:45 p.m. | L 16-5 | |
| Fri., 5/13 | JV Softball | Maloney | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | 3:45 p.m. | ||
| Sat., 5/14 | JV Baseball | Maloney | Home - Middletown HS-MHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/14 | V Softball | Bristol Central | Away - Bristol Central HS-Softball Field [Directions] | 11:00 a.m. | L 8-0 | |
| Sun., 5/15 | V Boys Crew | NOVICE REGATTA | Home - Boathouse [Directions] | 7:00 a.m. | ||
| Sun., 5/15 | V Girls Crew | NOVICE REGATTA | Home - Boathouse [Directions] | 7:00 a.m. | ||
| Mon., 5/16 | V Girls Lacrosse | Enfield | Away - Enfield HS-EHS TURF [Directions] | 4:00 p.m. | W 14-12 | |
| Mon., 5/16 | V Girls Tennis | Maloney | Home - Middletown Tennis Courts-Beman Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/17 | V Baseball | Bristol Central | Away - Muzzy Field-Baseball Diamond [Directions] | 6:30 p.m. | L 8-4 | |
| Tue., 5/17 | JV Baseball | Conard | Away - Sedgwick MS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Boys Golf | Platt | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 185 Maloney 241 Medalist: Matt Steuerwald 44 | |
| Tue., 5/17 | V Boys Outdoor Track | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Lewis Mills | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | Rocky Hill | Away - Rocky Hill HS-Softball Diamond [Directions] | 3:45 p.m. | L 7-4 | |
| Wed., 5/18 | V Baseball | Simsbury | Away - Memorial Park-90 Foot Diamond (Lighted) [Directions] | 3:45 p.m. | W 10-7 | |
| Wed., 5/18 | FR Baseball | Simsbury | Away - Town Forest Park-90 Foot Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/18 | V Girls Lacrosse | E.O. Smith | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | L 10-12 | |
| Wed., 5/18 | V Softball | RHAM | Home - Pat Kidney Field-Softball field [Directions] | 6:00 p.m. | L 3-9 | |
| Wed., 5/18 | JV Softball | RHAM | Home - Moody School-Smith Park 2 - 300 Country Club Road, Middletown, CT [Directions] | Postponed | ||
| Wed., 5/18 | V Girls Tennis | Bristol Eastern | Away - Bristol Eastern HS-Tennis Court [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 5/19 | V Boys Golf | Bristol Eastern | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 176 Bristol Eastern 213 Medalist: Andrew Dunn | |
| Thu., 5/19 | V Boys Lacrosse | Maloney-Platt | Away - Platt HS-Platt Turf field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Outdoor Track | Berlin | Away - Berlin HS-Biscoglio Track [Directions] | 3:45 p.m. | ||
| Thu., 5/19 | V Ultimate Frisbee | Avon | Home - Middletown HS-MHS Stadium [Directions] | 6:00 p.m. | Senior Night | |
| Thu., 5/19 | JV Ultimate Frisbee | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Lacrosse | Wethersfield | Home - Middletown HS-MHS Stadium [Directions] | 3:45 p.m. | L 5-15 | |
| Thu., 5/19 | V Girls Outdoor Track | Berlin | Away - Berlin HS-Biscoglio Track [Directions] | 3:45 p.m. | ||
| Thu., 5/19 | V Softball | Simsbury | Away - Simsbury Memorial Park [Directions] | 6:00 p.m. | W 8-4 | |
| Thu., 5/19 | JV Softball | Simsbury | Away - Simsbury Memorial Park [Directions] | 3:45 p.m. | ||
| Fri., 5/20 | V Baseball | Coginchaug | Home - Palmer Field-Baseball Diamond [Directions] | 3:45 p.m. | L 5-2 | |
| Fri., 5/20 | V Softball | Lewis Mills | Away - Lewis Mills HS-Softball Varsity Field [Directions] | 3:45 p.m. | W 9-2 | |
| Fri., 5/20 | V Girls Tennis | Lewis Mills | Home - Middletown Tennis Courts-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 5/21 | V Ultimate Frisbee | Hotchkiss | Away - Hotchkiss School | 9:00 a.m. | ||
| Sat., 5/21 | JV Ultimate Frisbee | Hotchkiss | Away - Hotchkiss School | 9:00 a.m. | ||
| Sun., 5/22 | V Co-ed Crew | CPSRA REGATTA (New Preston) | Home - Boathouse [Directions] | 9:00 a.m. | CPSRA REGATTA (New Preston) | |
| Mon., 5/23 | V Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - Varsity [Directions] | 3:45 p.m. | L 8-6 | |
| Mon., 5/23 | V Boys Lacrosse | Prince/Cheney Coop | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | W Forfeit | |
| Mon., 5/23 | V Girls Lacrosse | Enfield | Home - Middletown HS-MHS Stadium [Directions] | 5:15 p.m. | L 10-11 | |
| Tue., 5/24 | V Boys Golf | Windsor | Home - Lyman Orchards [Directions] | 3:00 p.m. | Middletown 170 Windsor 234 Medalist: Anthony Nanfito 40 | |
| Tue., 5/24 | V Boys Lacrosse | E.O. Smith | Home - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | CCC South Boys Track & Field | Away - Platt HS-Track | 3:45 p.m. | ||
| Tue., 5/24 | V Girls Outdoor Track | CCC South Girls Track & Field Meet | Away - Platt HS-Track | 3:45 p.m. | ||
| Wed., 5/25 | V Baseball | Newington | Home - Palmer Field-Baseball Diamond [Directions] | 6:30 p.m. | L 14-4 | |
| Wed., 5/25 | JV Baseball | Simsbury | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/25 | V Boys Lacrosse | Vinal-Goodwin | Home - Middletown HS-MHS Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/26 | V Baseball | Conard | Home - Middletown HS-MHS Baseball Field [Directions] | 3:45 p.m. | L 2-1 | |
| Thu., 5/26 | V Boys Golf | Plainville | Away - Hawks Landing County Club [Directions] | 3:00 p.m. | Middletown 162 Plainville 218 | |
| Fri., 5/27 | V Ultimate Frisbee | Newtown | Away - Newtown HS [Directions] | 4:00 p.m. | ||
| Fri., 5/27 | JV Ultimate Frisbee | Newtown | Away - Newtown HS [Directions] | 4:00 p.m. | ||
| Sat., 5/28 | V Co-ed Crew | Lewis Mills | Home - Boathouse [Directions] | 7:00 a.m. | Senior Day | |
| Tue., 5/31 | V Baseball | Platt | Away - Platt HS-Baseball Diamond [Directions] | 3:30 p.m. | W 6-4 | |
| Wed., 6/1 | V Baseball | Torrington | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:30 p.m. | W 5-4 | |
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Sat., 6/4 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | 12:00 p.m. | L 7-1 | |
| Sun., 6/5 | V Co-ed Crew | EMERSON REGATTA | Home - Boathouse [Directions] | 7:00 a.m. | EMERSON REGATTA | |
| Mon., 6/6 | V Boys Golf | CIAC Division I Spring Championship | Away - Stanley GC | 8:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||