(Featured Image: Paul Evans of Oval Ways)
| 1990-91 | Lex XI | ||
| 1991-92 | Lex XI | ||
| 1992–93 | Rhyl | ||
| 1993–94 | Welshpool Town | ||
| 1994–95 | Wrexham Reserves | ||
| 1995–96 | Oswestry Town | ||
| 1996–97 | Penrhyncoch | ||
| 1997–98 | Holywell Town | ||
| 1998–99 | Porthmadog | ||
| 1999–2000 | Welshpool Town | ||
| 2000–01 | Caernarfon Town | ||
| 2001–02 | Cemaes Bay | ||
| 2002–03 | Porthmadog | ||
| 2003–04 |  England | Buckley Town | |
| 2004–05 | England | COLIN CATON | Bala Town |
| 2005–06 | England | Glantraeth | |
| 2006–07 | England | COLIN CATON | Bala Town |
| 2007–08 | England | COLIN CATON | Bala Town |
| 2008–09 | England | COLIN CATON | Bala Town |
| 2009–10 | England | COLIN CATON | Llandudno |
| 2010–11 |  Wales | RUSSELL CADWALLADER | Guilsfield |
| 2011–12 | England | Rhyl | |
| 2012–13 | Conwy Borough | ||
| 2013–14 | Caernarfon Town | ||
| 2014–15 | Caersws | ||
| 2015–16 | Caernarfon Town | ||
| 2016–17 | Wales | IWAN WILLIAMS | Caernarfon Town |
| 2017–18 | Wales | SEAN EARDLEY | Flint Town United |
| 2018–19 | Wales | STEPHEN O’SHAUGHNESSY | Airbus UK Broughton |
