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
1/64-finals
1/32-finals
1/16-finals
1/8-finals
Quarter-finals
Semi-finals
Final
2019/20
1/64-finals
| 1 | Stenhousemuir | Bye | |
| 2 | Bye | Edinburgh City | |
| 4 | Bye | TNS | |
| 5 | Hearts U21 | Albion Rovers | 4 : 1 |
| 6 | Bye | Cowdenbeath | |
| 8 | Bye | Waterford | |
| 9 | Partick Thistle | Bye | |
| 11 | Forfar Athletic | Bye | |
| 12 | Bye | Montrose | |
| 13 | Cove Rangers | St Johnstone U21 | 4 : 1 |
| 14 | Aberdeen U21 | Brora Rangers | 0 : 6 |
| 16 | Bye | Connahs Q. | |
| 17 | Raith | Bye | |
| 18 | Fraserburgh | Ross County U21 | 2 : 3 |
| 19 | Celtic U21 | Queen's Park | 3 : 2 |
| 20 | Bye | Falkirk | |
| 21 | Formartine Utd | Livingston U21 | 3 : 1 |
| 22 | Bye | Peterhead | |
| 24 | Bye | Glenavon | |
| 25 | Airdrieonians | Bye | |
| 26 | Broomhill | Hamilton U21 | 0 : 4 |
| 28 | Bye | Bohemians | |
| 29 | Dundee FC | Bye | |
| 31 | Brechin | Bye | |
| 32 | Hibernian U21 | Elgin City | 3 : 4 |
| 33 | Inverness | Bye | |
| 36 | Bye | Morton | |
| 37 | Dunfermline | Bye | |
| 40 | Bye | Alloa | |
| 41 | Arbroath | Bye | |
| 44 | Bye | Dundee Utd | |
| 45 | Queen of South | Bye | |
| 47 | Motherwell U21 | Spartans | 1 : 0 |
| 48 | Bye | Clyde | |
| 49 | Solihull Moors | Bye | |
| 51 | Annan | Bye | |
| 52 | Kilmarnock U21 | Kelty Hearts | 0 : 4 |
| 53 | Ballymena | Bye | |
| 55 | Stranraer | Bye | |
| 56 | Berwick | Rangers U21 | 1 : 2 |
| 57 | Wrexham | Bye | |
| 60 | Bye | Ayr | |
| 61 | Stirling | Bye | |
| 62 | Bye | East Fife | |
| 63 | Dumbarton | Bye | |
| 64 | East Kilbride | St. Mirren U21 | 0 : 1 |
1/32-finals
| 1 | Stenhousemuir | Edinburgh City | 2 : 1 |
| 2 | Bye | TNS | |
| 3 | Hearts U21 | Cowdenbeath | 3 : 1 |
| 4 | Bye | Waterford | |
| 5 | Partick Thistle | Bye | |
| 6 | Forfar Athletic | Montrose | 1 : 2 |
| 7 | Cove Rangers | Brora Rangers | 2 : 1 |
| 8 | Bye | Connahs Q. | |
| 9 | Raith | Ross County U21 | 3 : 2 |
| 10 | Celtic U21 | Falkirk | 1 : 2 |
| 11 | Formartine Utd | Peterhead | 1 : 0 |
| 12 | Bye | Glenavon | |
| 13 | Airdrieonians | Hamilton U21 | 1 : 0 |
| 14 | Bye | Bohemians | |
| 15 | Dundee FC | Bye | |
| 16 | Brechin | Elgin City | 4 : 5 |
| 17 | Inverness | Bye | |
| 18 | Bye | Morton | |
| 19 | Dunfermline | Bye | |
| 20 | Bye | Alloa | |
| 21 | Arbroath | Bye | |
| 22 | Bye | Dundee Utd | |
| 23 | Queen of South | Bye | |
| 24 | Motherwell U21 | Clyde | 0 : 4 |
| 25 | Solihull Moors | Bye | |
| 26 | Annan | Kelty Hearts | 1 : 2 |
| 27 | Ballymena | Bye | |
| 28 | Stranraer | Rangers U21 | 0 : 2 |
| 29 | Wrexham | Bye | |
| 30 | Bye | Ayr | |
| 31 | Stirling | East Fife | 2 : 0 |
| 32 | Dumbarton | St. Mirren U21 | 0 : 1 |
1/16-finals
| 1 | Stenhousemuir | TNS | 2 : 1 |
| 2 | Hearts U21 | Waterford | 1 : 3 |
| 3 | Partick Thistle | Montrose | 2 : 0 |
| 4 | Cove Rangers | Connahs Q. | 0 : 1 |
| 5 | Raith | Falkirk | 2 : 0 |
| 6 | Formartine Utd | Glenavon | 0 : 3 |
| 7 | Airdrieonians | Bohemians | 3 : 2 |
| 8 | Dundee FC | Elgin City | 1 : 2 |
| 9 | Inverness | Morton | 3 : 1 |
| 10 | Dunfermline | Alloa | 1 : 2 |
| 11 | Arbroath | Dundee Utd | 1 : 0 |
| 12 | Queen of South | Clyde | 2 : 3 |
| 13 | Solihull Moors | Kelty Hearts | 2 : 1 |
| 14 | Ballymena | Rangers U21 | 0 : 1 |
| 15 | Wrexham | Ayr | 2 : 1 |
| 16 | Stirling | St. Mirren U21 | 0 : 1 |
1/8-finals
| 1 | Stenhousemuir | Waterford | 3 : 2 |
| 2 | Partick Thistle | Connahs Q. | 2 : 0 |
| 3 | Raith | Glenavon | 3 : 1 |
| 4 | Airdrieonians | Elgin City | 0 : 2 |
| 5 | Inverness | Alloa | 3 : 0 |
| 6 | Arbroath | Clyde | 0 : 2 |
| 7 | Solihull Moors | Rangers U21 | 3 : 4 |
| 8 | Wrexham | St. Mirren U21 | 4 : 1 |
Quarter-finals
| 1 | Stenhousemuir | Partick Thistle | 1 : 4 |
| 2 | Raith | Elgin City | 3 : 2 |
| 3 | Inverness | Clyde | 1 : 0 |
| 4 | Rangers U21 | Wrexham | 2 : 0 |
Semi-finals
| 1 | Partick Thistle | Raith | 1 : 2 |
| 2 | Inverness | Rangers U21 | 2 : 1 |
Final
| 1 | Raith | Inverness |
Social Media