Winning managers
| Final | Manager | Nationality | Club |
|---|---|---|---|
| 1877 | Selection committee | Wrexham | |
| 1878 | Newtown White Stars | ||
| 1879 | Druids | ||
| 1880 | Druids | ||
| 1881 | Druids | ||
| 1882 | Selection committee | Wrexham | |
| 1883 | Oswestry White Star | ||
| 1884 | Oswestry White Star | ||
| 1885 | Druids | ||
| 1886 | Druids | ||
| 1887 | Chirk AAA | ||
| 1888 | Chirk AAA | ||
| 1889 | Chirk AAA | ||
| 1890 | Chirk AAA | ||
| 1891 | Shrewsbury Town | ||
| 1892 | Chirk AAA | ||
| 1893 | Selection committee | Wrexham | |
| 1894 | Chirk AAA | ||
| 1895 | Newtown | ||
| 1896 | Bangor | ||
| 1897 | Selection committee | Wrexham | |
| 1898 | Druids | ||
| 1899 | Druids | ||
| 1900 | Aberystwyth Town | ||
| 1901 | Oswestry United | ||
| 1902 | Wellington Town | ||
| 1903 | Selection committee | Wrexham | |
| 1904 | Druids | ||
| 1905 | Selection committee | Wrexham | |
| 1906 | Wellington Town | ||
| 1907 | Oswestry United | ||
| 1908 | Selection committee | Chester | |
| 1909 | Selection committee | Wrexham | |
| 1910 | Selection committee | Wrexham | |
| 1911 | Selection committee | Wrexham | |
| 1912 | Fred Stewart |  England | Cardiff City |
| 1913 | Walter Whittaker | England | Swansea Town |
| 1914 | Selection committee | Wrexham | |
| 1915 | Selection committee | Wrexham | |
| 1920 | Fred Stewart | England | Cardiff City |
| 1921 | Selection committee | Wrexham | |
| 1922 | Fred Stewart | England | Cardiff City |
| 1923 | Fred Stewart | England | Cardiff City |
| 1924 | Selection committee | Wrexham | |
| 1925 | Charlie Hewitt | England | Wrexham |
| 1926 | Ebbw Vale | ||
| 1927 | Fred Stewart | England | Cardiff City |
| 1928 | Fred Stewart | England | Cardiff City |
| 1929 | England | Connah’s Quay & Shotton | |
| 1930 | Fred Stewart | England | Cardiff City |
| 1931 | Jack Baynes | England | Wrexham |
| 1932 | Jimmy Thomson | England | Swansea Town |
| 1933 | Charlie Hewitt | England | Chester |
| 1934 | Bob Hewison | England | Bristol City |
| 1935 | Jack Carr | England | Tranmere Rovers |
| 1936 | Tom Bailey | England | Crewe Alexandra |
| 1937 | Tom Bailey | England | Crewe Alexandra |
| 1938 | Ted Bousted | England | Shrewsbury Town |
| 1939 | South Liverpool | ||
| 1947 | Frank Brown | England | Chester |
| 1948 | Lovell’s Athletic | ||
| 1949 | Merthyr Tydfil | ||
| 1950 | Billy McCandless | Northern Ireland | Swansea Town |
| 1951 | Merthyr Tydfil | ||
| 1952 | John Dougary |  Scotland | Rhyl |
| 1953 | John Dougary | Scotland | Rhyl |
| 1954 | Billy Russel | Flint Town United | |
| 1955 | Basil Bright | 🏴 Wales | Barry Town |
| 1956 | Trevor Morris | 🏴 Wales | Cardiff City |
| 1957 | Cliff Lloyd | 🏴 Wales | Wrexham |
| 1958 | John Love | Scotland | Wrexham |
| 1959 | Bill Jones | 🏴 Wales | Cardiff City |
| 1960 | Billy Morris | 🏴 Wales | Wrexham |
| 1961 | Trevor Morris | 🏴 Wales | Swansea Town |
| 1962 | T. G. Jones | 🏴 Wales | Bangor City |
| 1963 | Borough United | ||
| 1964 | George Swindin | England | Cardiff City |
| 1965 | Jimmy Scoular | Scotland | Cardiff City |
| 1966 | Glyn Davis | 🏴 Wales | Swansea Town |
| 1967 | Jimmy Scoular | Scotland | Cardiff City |
| 1968 | Jimmy Scoular | Scotland | Cardiff City |
| 1969 | Jimmy Scoular | Scotland | Cardiff City |
| 1970 | Jimmy Scoular | Scotland | Cardiff City |
| 1971 | Jimmy Scoular | Scotland | Cardiff City |
| 1972 | John Neal | England | Wrexham |
| 1973 | Jimmy Scoular | Scotland | Cardiff City |
| 1974 | Frank O’Farrell |  Ireland | Cardiff City |
| 1975 | John Neal | England | Wrexham |
| 1976 | Jimmy Andrews | Scotland | Cardiff City |
| 1977 | Alan Durban | 🏴 Wales | Shrewsbury Town |
| 1978 | Arfon Griffiths | 🏴 Wales | Wrexham |
| 1979 | Graham Turner | England | Shrewsbury Town |
| 1980 | Len Ashurst | England | Newport County |
| 1981 | John Toshack | 🏴 Wales | Swansea City |
| 1982 | John Toshack | 🏴 Wales | Swansea City |
| 1983 | John Toshack | 🏴 Wales | Swansea City |
| 1984 | Graham Turner | England | Shrewsbury Town |
| 1985 | Chic Bates | England | Shrewsbury Town |
| 1986 | Dixie McNeil | England | Wrexham |
| 1987 | Lyn Jones | 🏴 Wales | Merthyr Tydfil |
| 1988 | Frank Burrows | Scotland | Cardiff City |
| 1989 | Ian Evans | 🏴 Wales | Swansea City |
| 1990 | Colin Addison | England | Hereford United |
| 1991 | Frank Burrows | Scotland | Swansea City |
| 1992 | Eddie May | England | Cardiff City |
| 1993 | Eddie May | England | Cardiff City |
| 1994 | Andy Beattie | Scotland | Barry Town |
| 1995 | Brian Flynn | 🏴 Wales | Wrexham |
| 1996 | Graham Breeze | 🏴 Wales | Llansantffraid |
| 1997 | Gary Barnett | England | Barry Town |
| 1998 | Graeme Sharp & John Hulse | Scotland England | Bangor City |
| 1999 | George Wood | Scotland | Inter Cable-Tel |
| 2000 | Meirion Appleton | 🏴 Wales | Bangor City |
| 2001 | Peter Nicholas | 🏴 Wales | Barry Town |
| 2002 | Kenny Brown | England | Barry Town |
| 2003 | Kenny Brown | England | Barry Town |
| 2004 | John Hulse | England | Rhyl |
| 2005 | Ken McKenna | England | The New Saints |
| 2006 | John Hulse | England | Rhyl |
| 2007 | Mark Jones | 🏴 Wales | Carmarthen Town |
| 2008 | Neville Powell | 🏴 Wales | Bangor City |
| 2009 | Neville Powell | 🏴 Wales | Bangor City |
| 2010 | Neville Powell | 🏴 Wales | Bangor City |
| 2011 | Andy Legg | 🏴 Wales | Llanelli |
| 2012 | Craig Harrison | England | The New Saints |
| 2013 | Neil Gibson | 🏴 Wales | Prestatyn Town |
| 2014 | Craig Harrison | England | The New Saints |
| 2015 | Craig Harrison | England | The New Saints |
| 2016 | Craig Harrison | England | The New Saints |
| 2017 | Colin Caton | England | Bala Town |
| 2018 | Andy Morrison | Scotland | Connah’s Quay Nomads |
| 2019 | Scott Ruscoe | England | The New Saints |
| 2022 | Anthony Limbrick | 🇦🇺 Australia | The New Saints |
| 2023 | Craig Harrison | England | The New Saints |
