| Season | Champion |
|---|---|
| 2023-24 | Glenbrook North Spartans (JV) |
| 2022-23 | York Dukes (JV) |
| 2021-22 | Glenbrook North Spartans (JV) |
| 2021 | York Dukes (JV) |
| 2019-20 | York Dukes (JV) |
| 2018-19 | York Dukes (JV) |
| 2017-18 | Loyola Ramblers (JV) |
| 2016-17 | Glenbrook North Spartans (JV) |
| 2015-16 | Glenbrook North Spartans (JV) |
| 2014-15 | New Trier Trevians (JV) |
| 2013-14 | Glenbrook North Spartans (JV) |
| 2012-13 | Glenbrook North Spartans (JV) |
Awarded to the team with the most regular season standings points
| Season | Trophy Winner |
|---|---|
| 2023-24 | Glenbrook North Spartans (JV) |
| 2022-23 | York Dukes (JV) |
| 2021-22 | Glenbrook North Spartans (JV) |
| 2021 | n/a |
| 2019-20 | York Dukes (JV) |
| 2018-19 | Stevenson Patriots |
| 2017-18 | Glenbrook North Spartans (JV) |
| 2016-17 | Loyola Ramblers (JV) |
| 2015-16 | New Trier Trevians (JV) |
| 2014-15 | New Trier Trevians (JV) |
| 2013-14 | Glenbrook North Spartans (JV) |
| 2012-13 | Glenbrook North Spartans (JV) |