2025/26 2024/25 2023/24 2022/23 2021/22 2019/20 2018/19 2017/18 2016/17 2015/16 2014/15 2013/14 2012/13 2011/12 2010/11 2009/10 2008/09 2007/08 2006/07 2005/06 2004/05
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2008/09
1/16-finals
| 1 | Airdrieonians | Dumbarton | 3 : 2 |
| 2 | Brechin | East Fife | 0 : 1 |
| 3 | Albion Rovers | Stenhousemuir | 1 : 0 |
| 4 | Elgin City | Cowdenbeath | 0 : 2 |
| 5 | Livingston | Stranraer | 4 : 0 |
| 6 | Arbroath | Forfar Athletic | 1 : 2 |
| 7 | Peterhead | Montrose | 6 : 0 |
| 8 | Queen's Park | Partick Thistle | 1 : 2 |
| 9 | Morton | Bye | |
| 10 | Ayr | East Stirlingshire | 1 : 2 |
| 11 | Dunfermline | Bye | |
| 12 | Berwick | Queen of South | 1 : 5 |
| 13 | Clyde | Gretna | 2 : 0 |
| 14 | Dundee FC | Alloa | 1 : 2 |
| 15 | Raith | Bye | |
| 16 | St Johnstone | Ross County | 1 : 2 |
1/8-finals
| 1 | Airdrieonians | East Fife | 3 : 0 |
| 2 | Albion Rovers | Cowdenbeath | 2 : 3 |
| 3 | Livingston | Forfar Athletic | 1 : 0 |
| 4 | Peterhead | Partick Thistle | 2 : 4 |
| 5 | Morton | East Stirlingshire | 3 : 0 |
| 6 | Dunfermline | Queen of South | 0 : 2 |
| 7 | Clyde | Alloa | 2 : 0 |
| 8 | Raith | Ross County | 1 : 2 |
Quarter-finals
| 1 | Airdrieonians | Cowdenbeath | 2 : 1 |
| 2 | Livingston | Partick Thistle | 0 : 2 |
| 3 | Morton | Queen of South | 2 : 0 |
| 4 | Clyde | Ross County | 0 : 1 |
Semi-finals
| 1 | Airdrieonians | Partick Thistle | 1 : 0 |
| 2 | Morton | Ross County | 1 : 4 |
Final
| 1 | Airdrieonians | Ross County | 3 : 2 |
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