| 08/25/2019 | Team 02 Hill (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 08/25/2019 | Team 05 Stried (Pee Wee Flag) | Team 03 Donehue (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 08/25/2019 | Team 08 Chitty (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 08/25/2019 | Team 07 Williams (Pee Wee Flag) | Team 06 Brown (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 09/01/2019 | Team 09 Primavera (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 09/01/2019 | Team 05 Stried (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 09/01/2019 | Team 06 Brown (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 09/01/2019 | Team 07 Williams (Pee Wee Flag) | Team 03 Donehue (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 09/08/2019 | Team 03 Donehue (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 09/08/2019 | Team 04 Bertagna (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 09/08/2019 | Team 08 Chitty (Pee Wee Flag) | Team 05 Stried (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 09/08/2019 | Team 09 Primavera (Pee Wee Flag) | Team 06 Brown (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 09/15/2019 | Team 04 Bertagna (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 09/15/2019 | Team 06 Brown (Pee Wee Flag) | Team 03 Donehue (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 09/15/2019 | Team 09 Primavera (Pee Wee Flag) | Team 07 Williams (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 09/15/2019 | Team 08 Chitty (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 09/22/2019 | Team 05 Stried (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 09/22/2019 | Team 07 Williams (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 09/22/2019 | Team 08 Chitty (Pee Wee Flag) | Team 03 Donehue (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 09/22/2019 | Team 09 Primavera (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 09/29/2019 | Team 08 Chitty (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 09/29/2019 | Team 09 Primavera (Pee Wee Flag) | Team 03 Donehue (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 09/29/2019 | Team 07 Williams (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 09/29/2019 | Team 06 Brown (Pee Wee Flag) | Team 05 Stried (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 10/06/2019 | Team 07 Williams (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 10/06/2019 | Team 09 Primavera (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 10/06/2019 | Team 08 Chitty (Pee Wee Flag) | Team 06 Brown (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 10/06/2019 | Team 05 Stried (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 10/13/2019 | Team 06 Brown (Pee Wee Flag) | Team 01 Conley (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 10/13/2019 | Team 03 Donehue (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 10/13/2019 | Team 08 Chitty (Pee Wee Flag) | Team 07 Williams (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 10/13/2019 | Team 09 Primavera (Pee Wee Flag) | Team 05 Stried (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |
| 10/20/2019 | Team 03 Donehue (Pee Wee Flag) | Team 04 Bertagna (Pee Wee Flag) | 12:00PM - 1:05PM | Berkshire MS / Stadium | |
| 10/20/2019 | Team 06 Brown (Pee Wee Flag) | Team 02 Hill (Pee Wee Flag) | 1:10PM - 2:15PM | Berkshire MS / Stadium | |
| 10/20/2019 | Team 05 Stried (Pee Wee Flag) | Team 07 Williams (Pee Wee Flag) | 2:20PM - 3:25PM | Berkshire MS / Stadium | |
| 10/20/2019 | Team 09 Primavera (Pee Wee Flag) | Team 08 Chitty (Pee Wee Flag) | 3:30PM - 4:40PM | Berkshire MS / Stadium | |