as Division Two (Tier 3 of the Welsh Football League)
| 1964-65 | Chepstow Town | ||
| 1965-66 | Caerleon | ||
| 1966-67 | Swansea University | ||
| 1967-68 | Cwmbran Town | ||
| 1968-69 | Ynysybwl Athletic | ||
| 1969-70 | Croesyceiliog | ||
| 1970-71 | Cardiff University | ||
| 1971-72 | Sully | ||
| 1972-73 | Pontllanfraith | ||
| 1973-74 | Caerau Athletic | ||
| 1974-75 | Blaenavon Blues | ||
| 1975-76 |  Wales | Abergavenny Thursdays | Abergavenny Thursdays |
| 1976-77 | Wales | Milford United | |
| 1977-78 | Aberaman Athletic | ||
| 1978-79 | Wales | Newport YMCA | |
| 1979-80 | Lake United | ||
| 1980-81 | Trelewis | ||
| 1981-82 | Wales | Ferndale Athletic | |
| 1982-83 | Tondu Robins |
as Division One (Tier 3 of the Welsh Football League)
| 1983-84 | Pontlottyn Blast Furnace | Pontlottyn Blast Furnace | |
|---|---|---|---|
| 1984-85 | Wales | Taffs Well | Taffs Well |
| 1985-86 | Wales | South Wales Police | South Wales Police |
| 1986-87 | Wales | BP (Llandarcy) | BP (Llandarcy) |
| 1987-88 | Merthyr Tydfil | Merthyr Tydfil | |
| 1988-89 | Garw Athletic | Garw Athletic | |
| 1989-90 | Wales | Caldicot Town | Caldicot Town |
as Division Two (Tier 3 of the Welsh Football League)
| 1990-91 | Wales | Cardiff Civil Service | Cardiff Civil Service |
|---|---|---|---|
| 1991-92 | Wales | AFC Porth | AFC Porth |
as Division Three (Tier 4 of the Welsh Football Pyramid)
| 1992–93 | Trowen Stars | ||
| 1993–94 | Penrhiwceiber Rangers | ||
| 1994–95 | Pontardawe Town | ||
| 1995–96 | Cardiff Institute | ||
| 1996–97 | Gwynfi United | ||
| 1997–98 | Ian Sturley | Milford United | |
| 1998–99 | Caerleon | ||
| 1999–2000 | Garw Athletic | ||
| 2000–01 | Bettws | ||
| 2001–02 | Newport YMCA | ||
| 2002–03 | Phil Preene & Alan Jacka | Pontyclun | |
| 2003–04 | Phil Clay | Bryntirion Athletic | |
| 2004–05 | Troedyrhiw | ||
| 2005–06 | West End | ||
| 2006–07 | Cwmbran Celtic | ||
| 2007–08 | Pentwyn Dynamo | ||
| 2008–09 | AFC Llwydcoed | ||
| 2009–10 | Aberbargoed Buds | ||
| 2010–11 | Monmouth Town | ||
| 2011–12 | Mark Crook | Undy Athletic | |
| 2012–13 | Wales | Dr Christian Edwards | Cardiff Metropolitan |
| 2013–14 | Wales | Gavin Chesterfield | Barry Town United |
| 2014–15 |  Scotland | Bob Jeffrey | Llanelli Town |
| 2015–16 | Wales | Damien & Dominic Broad | Pontypridd Town |
| 2016–17 | Wales | Karl Lewis | Llantwit Major |
| 2017–18 | Wales | Dafydd Evans | Swansea University |
| 2018–19 | Wales | Kerry Mullins | Penydarren BGC |
