| 19th Century |
| Season |
Winners (No.) |
Result |
Runner-up |
| 1889–90 | Tavistock (1) | 1–0 | Plymouth Town |
| 1890–91 | St. James the Less (1) | 2–1 | Plymouth United |
| 1891–92 | Plymouth (1) | –[note 2] | Plymouth United |
| 1892–93 | 7th CO WD Royal Artillery (1) | 2–0 | Bedford Regiment |
| 1893–94 | 7th CO WD Royal Artillery (2) | 3–1 | 2nd Battalion Devonshire Regiment |
| 1894–95 | 2nd Battalion Devonshire Regiment (1) | 2–1 | Somerset Light Infantry |
| 1895–96 | 1st Battalion Welch Regiment (1) | 2–0 | Royal Berkshire Regiment |
| 1896–97 | 2nd Battalion King's Own Royal Lancaster Regiment (1) | 3–0 | Gloucestershire Regiment |
| 1897–98 | 15th CO WD Royal Artillery (1) | 2–1 | Exeter United |
| 1898–99 | 1st Battalion Welch Regiment (2) | 2–1 | Argyle |
| 20th Century Pre-World War I |
| Season |
Winners (No.) |
Result |
Runner-up |
| 1899–1900 | Torpoint Athletic (1) | 1–0 | Argyle |
| 1900–01 | Devonport Royal Artillery (1) | 2–1 | Tavistock |
| 1901–02 | Greenwaves (1) | 3–0 | Argyle |
| 1902–03 | Argyle (1) | 3–0 | Tavistock |
| 1903–04 | Laira (1) | 2–0 | 1st Royal North Lancaster Regiment |
| 1904–05 | Greenwaves (2) | 2–0 | Duke of Cornwall's Light Infantry |
| 1905–06 | Plymouth Argyle reserves (2) | 8–1 | Oreston Rovers |
| 1906–07 | Plymouth Argyle reserves (3) | 1–0 | Royal Marines |
| 1907–08 | Plymouth Argyle reserves (4) | 2–1 | 3rd Rifles Brigade |
| 1908–09 | Royal Naval Barracks Devonport (1) | 3–2 | Plymouth Argyle |
| 1909–10 | 1st Battalion South Staffordshire Regiment (1) | 2–1 | Royal Garrison Artillery |
| 1910–11 | Torquay Town (1) | 2–0 | Royal Garrison Artillery |
| 1911–12 | Plymouth Argyle reserves (5) | 3–0 | Torquay Town |
| 1912–13 | Plymouth Argyle reserves (6) | 2–1 | Exeter City reserves |
| 1913–14 | Millbrook Rangers (1) | 1–0 | Plymouth Argyle reserves |
| 20th Century Post-World War I/Pre-World War II |
| Season |
Winners (No.) |
Result |
Runner-up |
| 1919–20 | No.3 Depot Royal Garrison Artillery (1) | 2–1 | Argyle |
| 1920–21 | Greenwaves (3) | 2–0 | Oreston Rovers |
| 1921–22 | Torquay United (1) | 1–0 | Oreston Rovers |
| 1922–23 | Plymouth St. Thomas (1) | 2–0 | Torquay United reserves |
| 1923–24 | Oreston Rovers (1) | 1–0 | Millbrook Rangers |
| 1924–25 | Oreston Rovers (2) | 4–1 | Friernhay |
| 1925–26 | Friernhay (1) | 2–1 | Royal Naval Barracks Devonport |
| 1926–27 | Royal Naval Barracks Devonport (2) | 3–1 | Tavistock |
| 1927–28 | Dartmouth United (1) | 3–2 | 2nd Hampshire Regiment |
| 1928–29 | Civil Service Plymouth (1) | 1–0 | Ilfracombe Town |
| 1929–30 | Greenwaves (4) | 2–0 | Ilfracombe Town |
| 1930–31 | Royal Marines (1) | 4–1 | Dartmouth United |
| 1931–32 | Royal Naval Barracks Devonport (3) | 5–2 | Devon General Exeter |
| 1932–33 | Devon General Exeter (1) | 2–1 | Dartmouth United |
| 1933–34 | Royal Naval Barracks Devonport (4) | 5–1 | Ilfracombe Town |
| 1934–35 | Friernhay (2) | 1–0 | Bideford United |
| 1935–36 | Friernhay (3) | 2–0 | Plymouth Civil Service |
| 1936–37 | Plymouth & Stoneouse Gas (1) | 3–0 | Bideford United |
| 1937–38 | Royal Naval Torpedos (1) | 2–1 | Friernhay |
| 1938–39 | Plymouth & Stoneouse Gas (2) | 4–0 | Dartmouth United |
| 1939–40 | Plymouth & Stoneouse Gas (3) | 2–1 | Ilfracombe Town |
| 20th Century Post-World War II |
| Season |
Winners (No.) |
Result |
Runner-up |
| 1945–46 | Plymouth United (1) | N/A | Royal Marines (1) |
| 1946–47 | Torquay United reserves (2) | 2–1 | Royal Naval Barracks Devonport |
| 1947–48 | Heavitree United (1) | 3–1 | Newton Abbot Spurs |
| 1948–49 | Dartmouth United (2) | 3–1 | Barnstaple Town |
| 1949–50 | Newton Abbot Spurs (1) | 3–1 | Tamerton |
| 1950–51 | Exmouth Town (1) | 1–1 † | Newton Abbot Spurs (1) |
| 1951–52 | Clyst Valley (1) | 4–2 | Callington |
| 1952–53 | Royal Naval Barracks Devonport (5) | 3–2 | Dartmouth United |
| 1953–54 | Holsworthy (1) | 3–2 | Dartmouth United |
| 1954–55 | Dartmouth United (3) | 5–1 | Friernhay |
| 1955–56 | Tiverton Town (3) | 3–2 | Tavistock |
| 1956–57 | Chelston (1) | 2–2 † | Plymouth United (2) |
| 1957–58 | Dawlish Town (1) | 4–3 | Dartmouth United |
| 1958–59 | Brixham United (1) | 5–1 | Tiverton Town |
| 1959–60 | Torquay United "A" (3) | 7–2 | Ottery St Mary |
| 1960–61 | Heavitree United (2) | 3–0 | Plymouth United |
| 1961–62 | Brixham United (2) | 1–0 | Cullompton Rangers |
| 1962–63 | Woodlands (1) | 3–0 | Newton Abbot Spurs |
| 1963–64 | Torquay United "A" (4) | 2–1 | Dawlish Town |
| 1964–65 | Portals Athletic (1) | 4–0 | Kingsteignton |
| 1965–66 | Tiverton Town (4) | 2–2 † | Upton Athletic (1) |
| 1966–67 | St Luke's College (1) | 4–3 | Dawlish Town |
| 1967–68 | Dawlish Town (2) | 3–1 | Holsworthy |
| 1968–69 | Tavistock (2) | 4–3 | Holsworthy |
| 1969–70 | Plymouth City (1) | 1–0 | Galmpton United |
| 1970–71 | Horrabridge United (1) | 2–0 | Millbridge |
| 1971–72 | Dolphin United (1) | 3–2 | Glampton United |
| 1972–73 | Brown & Sharpe (1) | 4–0 | Bideford |
| 1973–74 | Fawn United Plymouth (1) | 5–2 | Seaton Town |
| 1974–75 | Newton St Cyres (1) | 6–0 | BRSA Nomads (Plymouth) |
| 1975–76 | Bull Point (1) | 3–1 | Crownhill RBL |
| 1976–77 | Elmore (1) | 2–1 | Bideford AAC |
| 1977–78 | Tavistock United (1) | 5–1 | Topsham Town |
| 1978–79 | Sams United (1) | 4–2 | Dept. of Environment |
| 1979–80 | Bideford Center (1) | 2–1 | Fawn United |
| 1980–81 | Clyst Valley (2) | 6–1 | Ipplepen Athletic |
| 1981–82 | Tavistock (3) | 6–1 | Ipplepen Athletic |
| 1982–83 | Weston Mill Oak Villa reserves (1) | 5–1 | Greenbank |
| 1983–84 | Exeter Arms (1) | 2–1 | Appledore BAAC reserves |
| 1984–85 | Chelston (2) | 3–1 | City Engineers |
| 1985–86 | Willand Rovers (1) | 1–0 | Liverton United |
| 1986–87 | Varley Trophies (1) | 2–1 | Offwell Rangers |
| 1987–88 | Ottery St Mary (1) | 2–1 | Elmore reserves |
| 1988–89 | Exeter City Service (1) | 1–0 | Plymstock |
| 1989–90 | Buckfastleigh (1) | 3–0 | Ambrosia |
| 1990–91 | Newton Abbot Spurs (2) | 2–0 | Newton Abbot |
| 1991–92 | St Martins (1) | 1–0 | Falstaff Wanderers |
| 1992–93 | Barnstaple Town (1) | 2–0 | Vosper Oak Villa |
| 1993–94 | Cheriton Fitzpaine (1) | 3–1 | Barnstaple Town reserves |
| 1994–95 | Watts Blake Bearne (1) | 3–2 | Newton Abbot 66 |
| 1995–96 | Hooe St John (1) | 2–1 | Watts Blake Bearne |
| 1996–97 | Budleigh Salterton (1) | 6–2 | Watts Blake Bearne |
| 1997–98 | Combined 89 (1) | 5–1 | Hatherleigh Town |
| 1998–99 | Thorverton (1) | 2–1 | Elmore reserves |
| 21st Century |
| Season |
Winners (No.) |
Result |
Runner-up |
| 1999–2000 | Newton Abbot (1) | 2–1 | Barnstaple Town reserves |
| 2000–01 | Bideford reserves (1) | 6–1 | Compton Inn |
| 2001–02 | Barnstaple AAC (1) | 2–2 † ‡ | Willand Rovers |
| 2002–03 | Buckland Athletic reserves (1) | 3–2 | Princess Yachts International |
| 2003–04 | Heavitree Harriers (1) | 3–3 † ‡ | Morley Cars |
| 2004–05 | Kentisbeare (1) | 3–2 | Newton Abbot |
| 2005–06 | Upton Athletic reserves (1) | 1–0 | Bere Alston |
| 2006–07 | Combe Martin (1) | 3–1 | Lamerton |
| 2007–08 | Willand Rovers reserves (1) | 2–0 | Broadclyst |
| 2008–09 | Buckland Athletic reserves (2) | 1–0 | Lifton |
| 2009–10 | Buckland Athletic reserves (3) | 4–2 | Elburton Villa |
| 2010–11 | Loddiswell United (1) | 3–2 | Barnstaple |
| 2011–12 | Bow AAC (1) | 1–0 | Lee Moor |
| 2012–13 | Tiverton Town reserves (5) | 3–0 | Windmill |
| 2013–14 | Dartmouth (4) | 4–2 | Exwick Villa reserves |
| 2014–15 | Exwick Villa reserves (1) | 4–2 | Lapford |
| 2015–16 | University of Exeter reserves (1) | 4–2 | Lapford |
| 2016–17 | Cronies (1) | 3–0 | Roseland |
| 2017–18 | Sidmouth Town reserves (1) | 2–0 | Colyton |
| 2018–19 | Windwill reserves (1) | 2–2
(4–2 p.) † ‡ | Kentisbeare |
| 2019–20 | Thorverton (2) | 2–1 | Millbridge United |
| 2020–21 | Ottery St Mary reserves (2) | 4–1 | Northam Lions |
| 2021–22 | Kingsteignton Athletic (1) | 3–0 | Chudleigh Athletic |
| 2022–23 | University of Exeter reserves (2) | 3–0 | Newton St Cyres |
| 2023–24 | Newton Abbot Spurs reserves (4) | 3–1 | Paignton Saints |
52', 57'