Scottish Challenge Cup Results Scottish Football League Challenge Cup finals

| Season | Winner | Score | Runner_up | Venue | Attendance |
|---|---|---|---|---|---|
| 1998–99 | Competition suspended due to lack of sponsorship | Competition suspended due to lack of sponsorship | Competition suspended due to lack of sponsorship | Competition suspended due to lack of sponsorship | Competition suspended due to lack of sponsorship |
| 1999–2000 | Alloa Athletic | † 4–4 † | Inverness Caledonian Thistle | Excelsior Stadium | 4043 |
| 2000–01 | Airdrieonians | † 2–2 † | Livingston | Broadwood Stadium | 5623 |
| 2001–02 | Airdrieonians | 2–1 | Alloa Athletic | Broadwood Stadium | 4548 |
| 2002–03 | Queen of the South | 2–0 | Brechin City | Broadwood Stadium | 6428 |
| 2003–04 | Inverness Caledonian Thistle | 2–0 | Airdrie United | McDiarmid Park | 5428 |
| 2004–05 | Falkirk | 2–1 | Ross County | McDiarmid Park | 7471 |
| 2005–06 | St. Mirren | 2–1 | Hamilton Academical | Excelsior Stadium | 9613 |
| 2006–07 | Ross County | † 1–1 † | Clyde | McDiarmid Park | 4062 |
| 2007–08 | St. Johnstone | 3–2 | Dunfermline Athletic | Dens Park | 6446 |
| 2008–09 | Airdrie United | † 2–2 † | Ross County | McDiarmid Park | 4091 |