USL League Two
 
Final
St. Charles
Chicago City
SportsEngine Play
5
1
 
Final
Des Moines Menace
Chicago City
SportsEngine Play
4
1
 
Final
Chicago City
Chicago Dutch Lions
SportsEngine Play
0
3
 
Final
Chicago City
St. Charles
SportsEngine Play
0
0
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Chicago Dutch Lions
Chicago City
 
Bavarian United SC
Chicago City
 USL League Two
 
Final
Chicago City
Sueno
SportsEngine Play
1
5
 USL W League
 
Chicago City
Chicago Dutch Lions
 USL League Two
 
Final
Chicago City
Des Moines Menace
SportsEngine Play
0
2
 USL W League
 
Chicago City
Bavarian United SC
 USL League Two
 
Final
Chicago City
River Light
SportsEngine Play
1
3
 USL W League
 
Chicago City
RKC Third Coast
 
Final
Minnesota Aurora
Chicago City
4
1
 
Final
Chicago City
River Light
0
4
 USL League Two
 
Final
Chicago City
Peoria
SportsEngine Play
0
2
 
Final
Chicago Dutch Lions
Chicago City
SportsEngine Play
1
5
 USL W League
 
Final
Rochester
Chicago City
SportsEngine Play
3
2
 USL League Two
 
Final
Peoria
Chicago City
SportsEngine Play
4
1
 
Final
Sueno
Chicago City
SportsEngine Play
2
2
 
Final
River Light
Chicago City
SportsEngine Play
2
1