| Year | Winning Manager | Team Name | |
| 2010/11 | |||
| 2009/10 | Simon Baldwin | Agg O'Knee in Division 3 | (click here for details) |
| 2008/09 | Stevie G | Union Tavern | (click here for details) |
| 2007/08 | Tim Owen | When Saturday Comes | (click here for details) |
| 2006/07 | Patrick Williams | PEAS FC | |
| 2005/06 | Simon Baldwin | Shattered Dreams | |
| 2004/05 | Simon Waller | Boro Battlers | |
| 2003/04 | Jimmy Yates | Goldenballs |
