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Teams |
|
Status |
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| Brockton - Edgars Field | |
| 1 |
May | Sun |
10:00AM |
|
@ Brockton A's 6, Winchester Pirates 5 |
|
Final |
|
| Canton - Ruane Field | |
| 19 |
June | Sun |
9:00AM |
|
@ JM Force of Hyde Park 12, Winchester Pirates 2 |
|
Final |
|
| Chelsea - Chelsea HS | |
| 13 |
July | Wed |
8:00PM |
|
Milton Breakers 11 @ Winchester Pirates 3 |
|
Final |
|
| 20 |
July | Wed |
8:00PM |
|
Winchester Pirates 20 @ Boston Mets 6 |
|
Final |
|
| 17 |
Aug | Wed |
8:00PM |
|
@ Winchester Pirates 4, JM Force of Hyde Park 3 |
|
Final |
|
| 22 |
Aug | Mon |
8:00PM |
|
Weymouth Grays 3 @ Winchester Pirates 2 |
|
Final |
|
| 14 |
Sept | Wed |
8:00PM |
|
@ Winchester Pirates 4, Brockton A's 3 |
|
Final |
|
| Concord - Middlesex School | |
| 21 |
Aug | Sun |
10:00AM |
|
Winchester Pirates 14 @ Boston Braves 5 |
|
Final |
|
| East Boston - Sartori Stadium | |
| 6 |
May | Fri |
8:00PM |
|
@ Newton Red Sox 12, Winchester Pirates 8 |
|
Final |
|
| 3 |
Aug | Wed |
8:00PM |
|
Hyde Park Orioles 7 @ Winchester Pirates 1 |
|
Final |
|
| Haverhill - Haverhill Stadium | |
| 18 |
Aug | Thu |
8:00PM |
|
@ Boston Cardinals 2, Winchester Pirates 1 |
|
Final |
|
| Hyde Park - Kelly | |
| 22 |
May | Sun |
1:00PM |
|
@ Hyde Park Orioles 11, Winchester Pirates 7 |
|
Final |
|
| Lynn - Breed JHS Edmunds | |
| 10 |
Aug | Wed |
8:00PM |
|
@ North Shore Vipers 9, Winchester Pirates 4 |
|
Final |
|
| Reading - Austin Prep | |
| 26 |
June | Sun |
3:00PM |
|
Newton Red Sox 4 @ Winchester Pirates 0 |
|
Final |
|
| 10 |
July | Sun |
3:00PM |
|
@ Winchester Pirates 14, Boston Mets 8 |
|
Final |
|
| Roslindale - Fallon | |
| 12 |
May | Thu |
7:30PM |
|
@ Winchester Pirates 6, Boston Cardinals 5 |
|
Final |
|
| 15 |
Sept | Thu |
7:30PM |
|
@ Milton Breakers 7, Winchester Pirates 2 |
|
Final |
|
| Watertown - Moxley | |
| 11 |
Sept | Sun |
9:00AM |
|
Winchester Pirates 6 @ Middlesex Brewers 5 (1) |
|
Final |
|
| 11 |
Sept | Sun |
11:30AM |
|
@ Middlesex Brewers 11, Winchester Pirates 6 (2) |
|
Final |
|
| Weymouth - Libby Field | |
| 5 |
June | Sun |
10:00AM |
|
Winchester Pirates 14 @ Weymouth Grays 11 |
|
Final |
|
| Woburn - Leland Park | |
| 17 |
July | Sun |
3:00PM |
|
Boston Braves 6 @ Winchester Pirates 4 |
|
Final |
|
| 24 |
July | Sun |
10:00AM |
|
@ Winchester Pirates 3, North Shore Black Sox 2 (1) |
|
Final |
|
| 24 |
July | Sun |
12:30PM |
|
@ North Shore Black Sox 3, Winchester Pirates 2 (2) |
|
Final |
|
| 14 |
Aug | Sun |
2:00PM |
|
North Shore Vipers 10 @ Winchester Pirates 9 |
|
Final |
|