Montgomeryshire Challenge Cup

The Montgomeryshire Challenge Cup is a football knockout tournament involving teams from Mid Wales. The competition was established for the 1906–07 season. Caersws are the most successful club in the competition's history.

Previous winners

1900s

1906–07: – Royal Welsh Warehouse
1907–08: – Royal Welsh Warehouse
1908–09: – Montgomery Town
1909–10: – Llanidloes Town

1910s

1910–11: – Llanfyllin Town
1911–12: – Llanfyllin Town
1912–13: – Llanidloes Town
1913–14: – Royal Welsh Warehouse
1914–15: – No competition - World War One
1915–16: – No competition - World War One
1916–17: – No competition - World War One
1917–18: – No competition - World War One
1918–19: – No competition - World War One
1919–20: – Llanidloes Town

1920s

1920–21: – Llanidloes Town
1921–22: – Llanidloes Town
1922–23: – Newtown
1923–24: – Llanfyllin Town
1924–25: – Llanidloes Town
1925–26: – Llanymynech
1926–27: – Llanymynech
1927–28: – Llanidloes Town
1928–29: – Llanidloes Town
1929–30: – Llanidloes Town

1930s

1930–31: – Llanidloes Town
1931–32: – Llanidloes Town
1932–33: – Llanidloes Town
1933–34: – Llanidloes Town
1934–35: – Llanidloes Town
1935–36: – Llanymynech
1936–37: – Newtown
1937–38: – Machynlleth
1938–39: – Llanidloes Town
1939–40: – ''No competition - World War Two''

1940s

1940–41: – No competition - World War Two
1941–42: – No competition - World War Two
1942–43: – No competition - World War Two
1943–44: – No competition - World War Two
1944–45: – No competition - World War Two
1945–46: – Llanymynech Rovers
1946–47: – Llanidloes Town
1947–48: – Newtown
1948–49: – Llanidloes Town
1949–50: – Newtown

1950s

1950–51: – Welshpool
1951–52: – Newtown
1952–53: – Caersws
1953–54: – Llanidloes Town
1954–55: – Newtown
1955–56: – Newtown
1956–57: – Newtown
1957–58: – Newtown
1958–59: – Montgomery Town
1959–60: – Caersws

1960s

1960–61: – Llanymynech Rovers
1961–62: – Llanidloes Town
1962–63: – Caersws
1963–64: – Llanymynech Rovers
1964–65: – Llanidloes Town
1965–66: – Newtown
1966–67: – Newtown
1967–68: – Newtown
1968–69: – Newtown
1969–70: – Caersws

1970s

1970–71: – Caersws
1971–72: – Caersws
1972–73: – Llanidloes Town
1973–74: – Llanfechain
1974–75: – Caersws
1975–76: – Llanidloes Town
1976–77: – Caersws
1977–78: – Caersws
1978–79: – Newtown
1979–80: – Llanidloes Town

1980s

1980–81: – Montgomery Town
1981–82: – Newtown
1982–83: – Carno
1983–84: – Caersws
1984–85: – Caersws
1985–86: – Caersws
1986–87: – Caersws
1987–88: – Caersws
1988–89: – Caersws
1989–90: – Caersws

1990s

1990–91: – Caersws
1991–92: – Caersws
1992–93: – Waterloo Rovers
1993–94: – Caersws
1994–95: – Caersws
1995–96: – Newtown
1996–97: – Caersws
1997–98: – Caersws
1998–99: – Caersws
1999–2000: – Welshpool Town

2000s

2000–01: – Caersws
2001–02: – Caersws
2002–03: – Caersws
2003–04: – Caersws
2004–05: – Caersws
2005–06: – Caersws
2006–07: – Caersws
2007–08: – Carno
2008–09: – Newtown
2009–10: – Montgomery Town

2010s

2010–11: – Montgomery Town
2011–12: – Montgomery Town
2012–13: – Four Crosses
2013–14: – Carno
2014–15: – Llanfair United
2015–16: – Llanfair United
2016–17: – Llanfair United
2017–18: – Four Crosses
2018–19: – Llanrhaeadr
2019–20: – ''Competition abandoned due to Coronavirus pandemic''

2020s

2020–21: – No competition - Covid-19 pandemic
2021–22: – Llanidloes Town
2022–23: – Llanidloes Town
2023–24: – Llanidloes Town
2024–25: – Caersws

Number of cup wins by clubs