1900s • 1901–02:
Milford United • 1902–03: • 1903–04: Pembroke Dock • 1904–05: Milford Haven • 1905–06: 2nd Wiltshire Regiment • 1906–07: 2nd Wiltshire Regiment • 1907–08: Milford United • 1908–09: Milford United • 1909–10: Milford Priory Mission • 1910–11: • 1911–12: • 1912–13: • 1913–14: Milford Town '''A full list of the league's top flight champions since 1945–46 is as follows:'''
1940s • 1945–46: RA Manorbier • 1946–47: RNAS Dale • 1947–48: Milford United • 1948–49:
Pembroke Borough • 1959–50: Milford United
1950s • 1950–51:
Goodwick United • 1951–52:
Hakin United • 1952–53: RA Manorbier • 1953–54: RAF (Pembroke Dock) • 1954–55: Hakin United • 1955–56: RAF (Pembroke Dock) • 1956–57:
Narberth • 1957–58: Narberth • 1958–59: Narberth • 1959–60: Narberth
1960s • 1960–61:
Haverfordwest County • 1961–62:
Fishguard Sports • 1962–63: Milford United • 1963–64: Hakin United • 1964–65: Pembroke Borough • 1965–66: Fishguard Sports • 1966–67: Fishguard Sports • 1967–68:
St Clears • 1968–69: Hakin United • 1969–70: Fishguard Sports
1970s • 1970–71:
Carew • 1971–72: Fishguard Sports • 1972–73: Fishguard Sports • 1973–74: Fishguard Sports • 1974–75: Fishguard Sports • 1975–76: Fishguard Sports • 1976–77: Carew • 1977–78: Goodwick United • 1978–79:
Merlins Bridge • 1979–80: Merlins Bridge
1980s • 1980–81:
Johnston • 1981–82: Johnston • 1982–83: Johnston • 1983–84: New Hedges/Saundersfoot • 1984–85: Carew • 1985–86: New Hedges/Saundersfoot • 1986–87: Fishguard Sports • 1987–88: Merlins Bridge • 1988–89: Merlins Bridge • 1989–90: Fishguard Sports
1990s • 1990–91: Merlins Bridge • 1991–92: Narberth • 1992–93: Merlins Bridge • 1993–94: Goodwick United • 1994–95: Merlins Bridge • 1995–96: Merlins Bridge • 1996–97: Hakin United • 1997–98: Hakin United • 1998–99: Hakin United • 1999–2000: Hakin United
2000s • 2000–01: Hakin United • 2001–02: Hakin United • 2002–03: Hakin United • 2003–04:
Monkton Swifts • 2004–05: Monkton Swifts • 2005–06: Monkton Swifts • 2006–07: Monkton Swifts • 2007–08: Merlins Bridge • 2008–09: Hakin United • 2009–10: Merlins Bridge
2010s • 2010–11: Hakin United • 2011–12: Merlins Bridge • 2012–13: Hakin United • 2013–14: Hakin United • 2014–15: Hakin United • 2015–16: Goodwick United • 2016–17: Hakin United • 2017–18: Hakin United • 2018–19: Monkton Swifts • 2019–20: Hakin United
2020s • 2020–21:
Season void • 2021–22: Hakin United • 2022–23: Goodwick United • 2023–24: Goodwick United • 2024–25: Goodwick United • 2025–26: Hakin United
Number of titles by winning clubs (since 1945) •
Hakin United – 21 titles •
Fishguard Sports – 11 titles •
Merlins Bridge – 11 tiles •
Goodwick United – 7 titles •
Monkton Swifts – 5 titles •
Narberth – 5 titles •
Carew – 3 titles •
Johnston – 3 titles •
Milford United – 3 titles • New Hedges/Saundersfoot – 2 titles •
Pembroke Borough – 2 titles • RAF (Pembroke Dock) – 2 titles • RA Manorbier – 2 titles •
Haverfordwest County – 1 title • RNAS Dale – 1 title •
St Clears – 1 title ==Pembrokeshire Senior Cup==