| Year | South Side / Wrecking Crew | Owner | North Side / 12th Man / Legion of Doom | Owner | Division Titles | # |
|---|---|---|---|---|---|---|
| 1993 | Rush'n Attack | Matthew Rush | Milwaukee's Beast | Jeff Summers | Milwaukee's Beast | 15 |
| 1994 | Rush'n Attack | Matthew Rush | King's Krushers | Chad King | Rush'n Attack | 8 |
| 1995 | Rush'n Attack | Matthew Rush | La Raza | John Miranda | Terminators | 8 |
| 1996 | Black Sheep | Nick Patel | Gimme Head | Jason Head | Arizona Shockers | 6 |
| 1997 | Rush'n Attack | Matthew Rush | Dawg Pound | Mike Cleveland | Sweaty Yetis | 5 |
| 1998 | Valentino's Henchmen | Robert Valentino | HeadHunters | Jason Head | HeadHunters | 5 |
| 1999 | Terminators | Greg Wilcox | Highwaymen | Marty Smith | Da Ho' Train | 5 |
| 2000 | Milwaukee's Beast | Jeff Summers | Valentino's Henchmen | Robert Valentino | JetSuck | 4 |
| 2001 | Wild Irish Laddies | Chris Reeves | Highwaymen | Marty Smith | Hello Nasty | 4 |
| 2002 | Hello Nasty | Troy Tennyson | Valentino's Henchmen | Robert Valentino | Nuclear Wessels | 3 |
| 2003 | Milwaukee's Beast | Jeff Summers | Nuclear Wessels | John Wesselmann | Valentino's Henchmen | 3 |
| 2004 | Milwaukee's Beast | Jeff Summers | Naked Warriors | Patrick Sanchez | Wild Irish Laddies | 2 |
| 2005 | Hello Nasty | Troy Tennyson | HeadHunters | Jason Head | Nefarious Norsemen | 2 |
| 2006 | Milwaukee's Beast | Jeff Summers | Sweaty Yetis | Jason Hall | Highwaymen | 2 |
| 2007 | Rush'n Attack | Matthew Rush | Nuclear Wessels | John Wesselmann | The Vagitarians | 2 |
| 2008 | Terminators | Greg Wilcox | Sweaty Yetis | Jason Hall | Dawg Pound | 2 |
| 2009 | Milwaukee's Beast | Jeff Summers | Nefarious Norsemen | Patrick Sanchez | Park Bullies | 2 |
| 2010 | Hello Nasty | Troy Tennyson | Sweaty Yetis | Jason Hall | Black Sheep | 1 |
| 2011 | Milwaukee's Beast | Jeff Summers | Sweaty Yetis | Jason Hall | La Raza | 1 |
| 2012 | Milwaukee's Beast | Jeff Summers | Arizona Shockers | Josh Hayes | King's Krushers | 1 |
| 2013 | Terminators | Greg Wilcox | Arizona Shockers | Josh Hayes | Dirty Sanchez | 1 |
| 2014 | Terminators | Greg Wilcox | Sweaty Yetis | Jason Hall | ||
| 2015 | Milwaukee's Beast | Jeff Summers | Arizona Shockers | Josh Hayes | ||
| 2016 | Milwaukee's Beast | Jeff Summers | Arizona Shockers | Josh Hayes | Conference Titles | # |
| 2017 | Milwaukee's Beast | Jeff Summers | Da Ho' Train | Jason Farmer | Rush'n Attack | 3 |
| Nuclear Wessels | John Wesselmann | JetSuck | Ron Clair | Milwaukee's Beast | 2 | |
| 2018 | Rush'n Attack | Matthew Rush | JetSuck | Ron Clair | Terminators | 2 |
| Milwaukee's Beast | Jeff Summers | Da Ho' Train | Jason Farmer | JetSuck | 2 | |
| 2019 | Rush'n Attack | Matthew Rush | Dirty Sanchez | Jack Saber | Arizona Shockers | 2 |
| Milwaukee's Beast | Jeff Summers | JetSuck | Jason Farmer | Da Ho' Train | 1 | |
| 2020 | Terminators | Greg Wilcox | JetSuck | Ron Clair | Dirty Sanchez | 1 |
| Park Bullies | Nic Loyd | Da Ho' Train | Jason Farmer | The Vagitarians | 1 | |
| 2021 | Terminators | Greg Wilcox | Arizona Shockers | Josh Hayes | ||
| Milwaukee's Beast | Jeff Summers | Wild Irish Laddies | Chris Reeves | |||
| 2022 | Terminators | Greg Wilcox | HeadHunters | Jason Head | ||
| Hello Nasty | Troy Tennyson | The Vagitarians | Eric Garza | |||
| 2023 | Rush'n Attack | Matthew Rush | Arizona Shockers | Josh Hayes | ||
| Milwaukee's Beast | Jeff Summers | The Vagitarians | Eric Garza | |||
| 2024 | Terminators | Greg Wilcox | Da Ho' Train | Jason Farmer | HeadHunters | Jason Head |
| The Red Pots | 12th Man | Wrecking Crew | ||||
| 2025 | The Blue Monster | Michael Cleveland | Da Ho' Train | Jason Farmer | Park Bullies | Nic Loyd |
| The Red Pots | 12th Man | Wrecking Crew |
