| Season | Champion | Runner-up | Third Place | Fourth Place | Fifth Place | Date | Teams |
|---|
| 2013 | | | | | | 11/17/12 | |
| 2014 | | | | | | 11/23/13 | |
| 2015 | Adlai E. Stevenson High School JV (101) | Adlai E. Stevenson High School Varsity (104) | Munster High School Varsity (126) | Munster High School JV (134) | Naperville Central High School (246) | 11/22/14 | 42? |
| 2016 | | | | | | 11/21/15 | |
| 2017 | Adlai E. Stevenson High School Gold (210) | Adlai E. Stevenson High School Green (238) | Hinsdale Central High School Red (267) | Munster High School White (268) | Naperville Central High School Varsity (309) | 11/19/16 | 56 |
| 2018 | Adlai E. Stevenson High School Green (93) | Adlai E. Stevenson High School Gold (149) | Munster High School White (259) | Munster High School Red (277) | New Trier High School Blue (292) | 11/18/17 | 56 |
| 2019 | Adlai E. Stevenson High School Green (135) | Adlai E. Stevenson High School Gold (155) | New Trier High School Blue (178) | Neuqua Valley High School (256) | New Trier High School Green (290) | 11/17/18 | 56 |
| 2020 | Adlai E. Stevenson High School Green (126) | Naperville North High School Varsity (139) | Adlai E. Stevenson High School Gold (190) | Neuqua Valley High School Blue (217) | Marquette University High School (222) | 11/23/19 | 56 |
| 2021 | New Trier High School Grey (100) | Adlai E. Stevenson High School Green (144) | Marquette University High School Gold (148) | Naperville North High School Varsity (154) | Adlai E. Stevenson High School Gold (189) | 11/21/20 | 75 |
| 2022 | Adlai E. Stevenson High School Green (177) | Marquette University High School Polka Dot (192) | Munster High School Black (360) | Naperville North High School Varsity (399) | Adlai E. Stevenson High School Gold (442) | 11/20/21 | 89 |
| 2023 | Adlai E. Stevenson High School Green (143) | Marquette University High School Polka Dot (156) | Adlai E. Stevenson High School Gold (169) | New Trier High School Blue (194) | Naperville North High School Varsity (202) | 11/19/22 | 56 |
| 2024 | Marquette University High School Polka Dot (86) | New Trier High School Pickleball (118) | Adlai E. Stevenson High School Green (157) | New Trier High School Chessboxing (191) | Adlai E. Stevenson High School Gold (213) | 11/18/23 | 56 |
| 2025 | Adlai E. Stevenson High School Green (124) | Marquette University High School Navy (143) | Adlai E. Stevenson High School Gold (174) | New Trier High School Green (185) | Waubonsie Valley High School Green (305) | 11/23/24 | 58 |
