2026/27 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
2006/07
1/16-finals
| 1 | Clyde | Bye | |
| 2 | Peterhead | Montrose | 0 : 2 |
| 3 | Queen of South | Stranraer | 1 : 0 |
| 4 | Livingston | Ayr | 1 : 2 |
| 5 | St Johnstone | Raith | 3 : 1 |
| 6 | East Stirlingshire | Queen's Park | 0 : 5 |
| 7 | Cowdenbeath | Stirling | 4 : 0 |
| 8 | Dumbarton | Morton | 1 : 2 |
| 9 | Albion Rovers | Partick Thistle | 2 : 1 |
| 10 | Stenhousemuir | Elgin City | 0 : 2 |
| 11 | Forfar Athletic | Dundee FC | 2 : 1 |
| 12 | Brechin | Arbroath | 1 : 2 |
| 13 | Gretna | Airdrieonians | 3 : 0 |
| 14 | Berwick | Hamilton | 1 : 3 |
| 15 | Alloa | Bye | |
| 16 | East Fife | Ross County | 0 : 3 |
1/8-finals
| 1 | Clyde | Montrose | 3 : 0 |
| 2 | Queen of South | Ayr | 2 : 3 |
| 3 | St Johnstone | Queen's Park | 3 : 0 |
| 4 | Cowdenbeath | Morton | 2 : 3 |
| 5 | Albion Rovers | Elgin City | 5 : 2 |
| 6 | Forfar Athletic | Arbroath | 1 : 3 |
| 7 | Gretna | Hamilton | 3 : 1 |
| 8 | Alloa | Ross County | 1 : 2 |
Quarter-finals
| 1 | Clyde | Ayr | 1 : 0 |
| 2 | St Johnstone | Morton | 2 : 3 |
| 3 | Albion Rovers | Arbroath | 4 : 3 |
| 4 | Gretna | Ross County | 2 : 3 |
Semi-finals
| 1 | Clyde | Morton | 3 : 1 |
| 2 | Albion Rovers | Ross County | 1 : 4 |
Final
| 1 | Clyde | Ross County | 1 : 2 |
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