| Year | Winning Manager | Team Name |
| 2023/24 | ||
| 2022/23 | Harry Baldwin | Marsching on together |
| 2021/22 | Chris Gerrard | Yann Sommer of '69 |
| 2020/21 | Colin Rigby (3) | Ascot Albion |
| 2019/20 | Colin Rigby (2) | Ascot Albion |
| 2018/19 | Graham Jeffries (3) | Going on a League 2 Tour |
| 2017/18 | Graham Highton | Barnstoneworth Utd |
| 2016/17 | Craig Frost | InterPenguins |
| 2015/16 | Matt Wakeman (Paul Keech) | Hercules & Chaddy |
| 2014/15 | Ian Cowburn | FC Lamborghini |
| 2013/14 | Owen Griffiths | Vive La Revolution |
| 2012/13 | Paul Gerrard | Adhesive Duck Deficiency |
| 2011/12 | Graham Jeffries (2) | Tottyboy |
| 2010/11 | Graham Jeffries | Tottyboy |
| 2009/10 | Rob Bushell | Robbies Foulers |
| 2008/09 | Paul Keech/Craig Frost | Exactly where predicted |
| 2007/08 | Colin Rigby | Ascot Albion |
| 2006/07 | Paul Keech (2) | Latic Attack |
| 2005/06 | Tim Owen (3) | Lost Weekend |
| 2004/05 | Simon Waller | Boro Battlers |
| 2003/04 | Stu Jones | I cant get a Ticket FC |
| 2002/03 | Ken Trainer (2) | KAST Utd |
| 2001/02 | Mark Jones | Scorchers |
| 2000/01 | Alan Keech | Oldham Roughyeds |
| 1999/00 | Tim Owen (2) | `The Bottler' |
| 1998/99 | Paul Keech | Latic Attack |
| 1997/98 | Russ Farnham | Watford Wonders |
| 1996/97 | Ken Trainer | KAST Utd |
| 1995/96 | Tim Owen | Mission Impossible |
| 1994/95 | Lynne Stokoe | (No Team Names) |
