US Open Cup
 
MS
Western Mass Pioneers
Union Omaha
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0
4
 USL League Two
 
MS
Boston Bolts
Western Mass Pioneers
0
1
 
MS
Western Mass Pioneers
Pathfinder
SportsEngine Play
4
0
 
MS
Blackwatch Rush
Western Mass Pioneers
SportsEngine Play
0
4
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Western Mass Pioneers
Black Rock
SportsEngine Play
5
0
 
MS
Western Mass Pioneers
Seacoast United Phantoms
SportsEngine Play
2
3
 
MS
Western Mass Pioneers
AC Connecticut
SportsEngine Play
5
0
 
MS
Vermont Green
Western Mass Pioneers
SportsEngine Play
0
0
 
MS
Pathfinder
Western Mass Pioneers
SportsEngine Play
0
2
 
MS
Western Mass Pioneers
Boston City
SportsEngine Play
6
1
 
MS
Western Mass Pioneers
Blackwatch Rush
SportsEngine Play
4
1
 
MS
Black Rock
Western Mass Pioneers
SportsEngine Play
0
1
 
MS
Boston City
Western Mass Pioneers
SportsEngine Play
0
5
 
MS
AC Connecticut
Western Mass Pioneers
SportsEngine Play
0
3
 
MS
Western Mass Pioneers
Vermont Green
SportsEngine Play
1
3
 
MS
Western Mass Pioneers
FC Motown II
SportsEngine Play
3
1
 
MS
Lionsbridge
Western Mass Pioneers
SportsEngine Play
2
1