Performance by individual
| Season | Nationality | Manager | Club |
|---|---|---|---|
| 1992–93 | 🏴 Wales | Tony Wilcox | Cwmbran Town |
| 1993–94 |  England | Nigel Adkins | Bangor City |
| 1994–95 | England | Nigel Adkins | Bangor City |
| 1995–96 | 🏴 Wales | Paul Giles | Barry Town |
| 1996–97 | England | Gary Barnett | Barry Town |
| 1997–98 | England | Gary Barnett | Barry Town |
| 1998–99 | England | Gary Barnett | Barry Town |
| 1999–00 | England | Andy Cale | The New Saints |
| 2000–01 | 🏴 Wales | Peter Nicholas | Barry Town |
| 2001–02 | England | Kenny Brown | Barry Town |
| 2002–03 | England | Kenny Brown | Barry Town |
| 2003–04 | England | John Hulse | Rhyl |
| 2004–05 | England | Ken McKenna | The New Saints |
| 2005–06 | England | Ken McKenna | The New Saints |
| 2006–07 | England | Ken McKenna | The New Saints |
| 2007–08 | 🏴 Wales | Peter Nicholas | Llanelli |
| 2008–09 | 🏴 Wales | Alan Bickerstaff | Rhyl |
| 2009–10 | England | Andy Cale | The New Saints |
| 2010–11 | 🏴 Wales | Neville Powell | Bangor City |
| 2011–12 | England | Craig Harrison | The New Saints |
| 2012–13 | England | Craig Harrison | The New Saints |
| 2013–14 | England | Craig Harrison | The New Saints |
| 2014–15 | England | Craig Harrison | The New Saints |
| 2015–16 | England | Craig Harrison | The New Saints |
| 2016–17 | England | Craig Harrison | The New Saints |
| 2017–18 | England | Scott Ruscoe | The New Saints |
| 2018–19 | England | Scott Ruscoe | The New Saints |
| 2019-20 |  Scotland | Andy Morrison | Connah’s Quay |
| 2020/21 | Scotland | Andy Morrison | Connah’s Quay |
| 2021/22 | 🇦🇺 Australia | Anthony Limbrick | The New Saints |
| Rank | Name | Winners | Club(s) | Winning seasons |
|---|---|---|---|---|
| 1 | Craig Harrison | 6 | The New Saints | 2011-12, 2012-13, 2013-14, 2014-15, 2015-16, 2016-17 |
| 2 | Gary Barnett | 3 | Barry Town United | 1996-97, 1997-98, 1998-99 |
| = | Ken McKenna | 3 | The New Saints | 2004-05, 2005-06, 2006-07 |
| 4 | Nigel Adkins | 2 | Bangor City | 1993-94, 1994-95 |
| = | Scott Ruscoe | 2 | The New Saints | 2017-18, 2018-19 |
| = | Peter Nicholas | 2 | Barry Town, Llanelli | 2000-01, 2007-08 |
| = | Kenny Brown | 2 | Barry Town | 2001-02, 2002-03 |
| = | Andy Morrison | 2 | Connah’s Quay | 2019-20, 2020/21 |
| 8 | Tony Wilcox | 1 | Cwmbran Town | 1992-93 |
| = | Andy Cale | 1 | The New Saints | 1990-00 |
| = | Neville Powell | 1 | Bangor City | 2010-11 |
| = | Alan Bickerstaff | 1 | Rhyl | 2008-09 |
| = | John Hulse | 1 | Rhyl | 2003-04 |
| = | Paul Giles | 1 | Barry Town | 1995-96 |
| = | Anthony Limbrick | 1 | The New Saints | 2021/22 |
