Chicago Perspectives 61, Belvidere 55
Rockford Jefferson 69, Chicago Perspectives 47
Chicago Perspectives 45, Freeport 43
Rockford Guilford 61, Chicago Perspectives 47
2018
Rockford Guilford 60, Chicago Perspectives 45
Chicago Hyde Park 71, Chicago Perspectives 36
Chicago Perspectives 52, Freeport 45
Rockford Jefferson 51, Chicago Perspectives 44
2019
Rockford Guilford 63, Chicago Perspectives 54
Chicago Perspectives 66, Elgin Larkin 64
Rockford Jefferson 64, Chicago Perspectives 60 (OT)
Machesney Park Harlem 54, Chicago Perspectives 53 (OT)
Second team All-Classic: Caleb Miller
2021
Rockford Auburn 54, Chicago Perspectives 33
Machesney Park Harlem 65, Chicago Perspectives 60
Rockford Jefferson 43, Chicago Perspectives 40
Rockford East 70, Chicago Perspectives 43
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