| Founded | 1905 |
|---|---|
| Abolished | 1963 |
| Region | Eastern Scotland |
| Most championships | Raith Rovers (8 titles) |
The Penman Cup was a Scottish association football knockout competition, played from 1906 to the 1960s.
George Penman, a Fifeshire businessman and director of Cowdenbeath, created the trophy for clubs from the counties of Fifeshire, Stirlingshire, Clackmannanshire, and Linlithgowshire, and in the East of Scotland Football Association, as an extra attraction towards the end of football seasons. A number of clubs attended a meeting at the Union Hotel, Dunfermline, on Saturday 23 December 1905, to inaugurate the tournament; ultimately, 19 teams were accepted as entrants, West Calder and Berwick Rangers having their applications refused. The relevant associations (both national and local) gave their approval in February 1906 and the competition was hailed as being of near-equal importance to the Scottish Qualifying Cup.
Given the donor was from Cowdenbeath, the Miners' ground at North End Park was used as the venue for the initial final tie, and Raith Rovers took the first title, beating Alloa Athletic 3–1 on 12 May 1906, the match being defined by two penalties; Raith scored first from the spot, but Alloa missed one soon afterwards.
The First World War interrupted the competition; the 1914–15 final between East Stirlingshire and Alloa Athletic was never played, as the committee disqualified any club which had not played off its scheduled rounds by 1 May, which left only the Shire and Alloa, but the committee then fixed the final to take place in Falkirk on 1 May itself. This caused problems for the Shire, as the Stirlingshire Cup consolation final had been scheduled for the same day. Alloa refused consent to play on another date without a guarantee of travelling expenses, which was not forthcoming; the Cup was therefore held over to the following season, but the war prevented the final from being played off.
In 1917, with entries diminished due to the First World War, and the 1916–17 competition not finishing until February 1918, the committee invited clubs from Perthshire and Forfarshire to boost numbers. This invitation lasted until the 1937–38 season - that season St Johnstone did not enter, but Dundee and Dundee United were drawn together in the first round - when, following a complaint from Raith and East Fife, the Scottish Football Association ruled clubs from those counties could not compete. The Penman Cup committee altered its rules formally to allow clubs from the counties to fall within the competition's reach but it was to no avail as the Scottish FA doubled down on the ban, with Leith Athletic and St Bernards joining the competition in their stead.
After the Second World War, increased league commitments meant the competition often did not reach a conclusion. After the 1961–62 competition was not completed until October 1962 (and even then runner-up Stirling Albion fielded six reserves in the final), and the 1962–63 competition had only had three games played by May, the competition was abandoned, and the trophy used for Fifeshire juvenile teams.
| Season | Winner | Score | Runners Up | Venue |
|---|---|---|---|---|
| 1905–06 | Raith Rovers (1) | 3–1 | Alloa Athletic | North End Park |
| 1906–07 | Bathgate (1) | 3–3, 3–2 | Broxburn Athletic | North End Park, Boghead Park |
| 1907–08 | St Bernard's (1) | 1–0 | East Stirlingshire | Brockville Park |
| 1908–09 | Raith Rovers (2) | 3–1 | Alloa Athletic | North End Park |
| 1909–10 | East Fife (1) | 1–1, 3–3. 2–1 | Stenhousemuir | North End Park, Recreation Park, Brockville Park |
| 1910–11 | Cowdenbeath (1) | 3–0 | Dunfermline Athletic | North End Park |
| 1911–12 | Raith Rovers (3) | 0–0, 4–1 | East Fife | Stark's Park |
| 1912–13 | Armadale (1) | 2–1 | Cowdenbeath | North End Park |
| 1913–14 | Broxburn United (1) | 3–2 | East Stirlingshire | Merchiston Park |
| 1914–15 | unfinished | |||
| 1915–16 | Cowdenbeath (2) | 5–1 | Bathgate | North End Park |
| 1916–17 | East Fife (2) | 1–0 | Armadale | North End Park |
| 1917–18 | Dundee (1) | 2–0 | Dundee Hibernian | Dens Park |
| 1918–19 | no competition | |||
| 1919–20 | Cowdenbeath (3) | 3–1 | Dunfermline Athletic | Central Park |
| 1920–21 | Alloa Athletic (1) | 2–0 | Dundee Hibernian | East End Park |
| 1921–22 | Dundee (2) | 3–1 | Raith Rovers | Dens Park |
| 1922–23 | Raith Rovers (4) | 1–0 | Dundee | Stark's Park |
| 1923–24 | Raith Rovers (5) | 3–2 | St Johnstone | Stark's Park |
| 1924–25 | no competition | |||
| 1925–26 | St Johnstone (1) | 2–2, 3–1 | Lochgelly United | East End Park, Muirton Park |
| 1926–27 | Alloa Athletic (2) | 2–0 | Raith Rovers | Stark's Park |
| 1927–28 | no competition | |||
| 1928–29 | Dundee (3) | 5–1 | Dundee United | Dens Park |
| 1929–30 | unfinished | |||
| 1930–31 | unfinished | |||
| 1931–32 | unfinished | |||
| 1932–33 | unfinished | |||
| 1933–34 | unfinished | |||
| 1934–35 | no competition | |||
| 1935–36 | unfinished | |||
| 1936–37 | Raith Rovers (6) | 2–0 | Alloa Athletic | Stark's Park |
| 1937–38 | unfinished | |||
| 1938–39 | East Fife (3) | 5–1 | Stenhousemuir | Bayview Park |
| 1939–40 | unfinished | |||
| 1933–34 | unfinished | |||
| 1940–45 | no competition | |||
| 1945–46 | unfinished | |||
| 1946–47 | unfinished | |||
| 1947–48 | Raith Rovers (7) | 2–1 | Heart of Midlothian | Tynecastle Park |
| 1948–49 | unfinished | |||
| 1949–50 | Stirling Albion (1) | 2–0 | Leith Athletic | Annfield |
| 1950–51 | unfinished | |||
| 1951–52 | unfinished | |||
| 1952–53 | unfinished | |||
| 1953–54 | Stenhousemuir (1) | 4–2 | Heart of Midlothian | Tynecastle Park |
| 1954–55 | unfinished | |||
| 1955–56 | unfinished | |||
| 1956–57 | Stirling Albion (2) | walkover | Alloa Athletic | |
| 1957–58 | Stirling Albion (3) | 5–0 | Raith Rovers | Annfield |
| 1958–59 | Raith Rovers (8) | 5–2 | East Stirlingshire | Stark's Park |
| 1959–60 | Dunfermline Athletic (1) | 3–0 | Stirling Albion | East End Park |
| 1960–61 | unfinished | |||
| 1961–62 | East Fife (4) | 3–1 | Stirling Albion | Bayview Park |
| 1962–63 | unfinished | |||