# 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. The current holders Llanidloes Town won the competition for the 24th time in the 2023–24 season.

## Previous winners
### 1900s

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

### 1910s

* 1910–11: – Llanfyllin Town
* 1911–12: – Llanfyllin Town
* 1912–13: –
* 1913–14: – Royal Welsh Warehouse Recreation
* 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: –

### 1920s

* 1920–21: –
* 1921–22: –
* 1922–23: –
* 1923–24: – Llanfyllin Town
* 1924–25: –
* 1925–26: – Llanmynech
* 1926–27: – Llanmynech
* 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: – Llanmynech
* 1936–37: – Newtown
* 1937–38: –
* 1938–39: –
* 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: – Llanmynech 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: – Llanmynech Rovers
* 1961–62: – Llanidloes Town
* 1962–63: – Caersws
* 1963–64: – Llanmynech 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: – Caersws
* 1983–84: – Caersws
* 1984–85: – Caersws
* 1985–86: – Caersws
* 1986–87: – Caersws
* 1989–88: – Caersws
* 1988–89: – Caersws
* 1989–90: – Caersws

### 1990s

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

### 2000s

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

### 2010s

* 2010–11: –
* 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: – Llanrhaedr
* 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