| 1990–91 | Dundee | 3–2 | Ayr United | Fir Park |
| 1991–92 | Hamilton Academical | 1–0 | Ayr United | Fir Park |
| 1992–93 | Hamilton Academical | 3–2 | Morton | Love Street |
| 1993–94 | Falkirk | 3–0 | St Mirren | Fir Park |
| 1994–95 | Airdrieonians | 3–2 | Dundee | McDiarmid Park |
| 1995–96 | Stenhousemuir | 0–0 | Dundee United | McDiarmid Park |
| 1996–97 | Stranraer | 1–0 | St Johnstone | Broadwood Stadium |
| 1997–98 | Falkirk | 1–0 | Queen of the South | Fir Park |
| 1998–99 | Competition suspended due to lack of sponsorship | | | |
| 1999–2000 | Alloa Athletic | 4–4 | Inverness Caledonian Thistle | Excelsior Stadium |
| 2000–01 | Airdrieonians | 2–2 | Livingston | Broadwood Stadium |
| 2001–02 | Airdrieonians | 2–1 | Alloa Athletic | Broadwood Stadium |
| 2002–03 | Queen of the South | 2–0 | Brechin City | Broadwood Stadium |
| 2003–04 | Inverness Caledonian Thistle | 2–0 | Airdrie United | McDiarmid Park |
| 2004–05 | Falkirk | 2–1 | Ross County | McDiarmid Park |
| 2005–06 | St Mirren | 2–1 | Hamilton Academical | Excelsior Stadium |
| 2006–07 | Ross County | 1–1 | Clyde | McDiarmid Park |
| 2007–08 | St Johnstone | 3–2 | Dunfermline Athletic | Dens Park |
| 2008–09 | Airdrie United | 2–2 | Ross County | McDiarmid Park |
| 2009–10 | Dundee | 3–2 | Inverness Caledonian Thistle | McDiarmid Park |
| 2010–11 | Ross County | 2–0 | Queen of the South | McDiarmid Park |
| 2011–12 | Falkirk | 1–0 | Hamilton Academical | Almondvale Stadium |
| 2012–13 | Queen of the South | 1–1 | Partick Thistle | Almondvale Stadium |
| 2013–14 | Raith Rovers | 1–0 | Rangers | Easter Road |
| 2014–15 | Livingston | 4–0 | Alloa Athletic | McDiarmid Park |
| 2015–16 | Rangers | 4–0 | Peterhead | Hampden Park |
| 2016–17 | Dundee United | 2–1 | St Mirren | Fir Park |
| 2017–18 | Inverness Caledonian Thistle | 1–0 | Dumbarton | McDiarmid Park |
| 2018–19 | Ross County | 3–1 | Connah's Quay Nomads | Caledonian Stadium |
