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
Draw
2024/251/64-finals
| 1 | Stranraer | Bye | |
| 2 | Bye | Bonnyrigg Rose | |
| 4 | Bye | Annan | |
| 5 | Queen's Park | Bye | |
| 8 | Bye | Edinburgh City | |
| 9 | Clyde | Bye | |
| 10 | Rangers B | Bo'ness United | 3 : 1 |
| 11 | Fraserburgh | Hearts B | 2 : 1 |
| 12 | Bye | Forfar Athletic | |
| 13 | Stenhousemuir | Bye | |
| 16 | Bye | Falkirk | |
| 17 | Queen of South | Bye | |
| 20 | Bye | Airdrieonians | |
| 21 | Motherwell B | East Stirlingshire | 0 : 1 |
| 22 | East Kilbride | Celtic B | 3 : 0 |
| 24 | Bye | Cove Rangers | |
| 25 | Ayr | Bye | |
| 28 | Bye | Raith | |
| 29 | Peterhead | Bye | |
| 31 | Dumbarton | Bye | |
| 32 | Berwick | St. Mirren B | 3 : 0 |
| 33 | East Fife | Bye | |
| 34 | St Johnstone B | Brechin | 2 : 1 |
| 36 | Bye | Dunfermline | |
| 37 | Kelty Hearts | Bye | |
| 39 | Elgin City | Bye | |
| 40 | Banks O' Dee | Aberdeen B | 1 : 0 |
| 41 | Partick Thistle | Bye | |
| 44 | Bye | Alloa | |
| 45 | Arbroath | Bye | |
| 48 | Bye | Montrose | |
| 49 | Spartans | Bye | |
| 52 | Bye | Livingston | |
| 53 | Inverness | Bye | |
| 56 | Bye | Stirling | |
| 57 | Hamilton | Bye | |
| 59 | Buckie Thistle | Dundee Utd B | 1 : 3 |
| 60 | Dundee FC B | Formartine Utd | 2 : 0 |
| 61 | Hibernian B | Albion Rovers | 3 : 4 |
| 62 | Cowdenbeath | Kilmarnock B | 4 : 2 |
| 64 | Bye | Morton |
1/32-finals
| 1 | Stranraer | Bonnyrigg Rose | 2 : 1 |
| 2 | Bye | Annan | |
| 3 | Queen's Park | Bye | |
| 4 | Bye | Edinburgh City | |
| 5 | Clyde | Rangers B | 2 : 3 |
| 6 | Fraserburgh | Forfar Athletic | 2 : 1 |
| 7 | Stenhousemuir | Bye | |
| 8 | Bye | Falkirk | |
| 9 | Queen of South | Bye | |
| 10 | Bye | Airdrieonians | |
| 11 | East Stirlingshire | East Kilbride | 2 : 3 |
| 12 | Bye | Cove Rangers | |
| 13 | Ayr | Bye | |
| 14 | Bye | Raith | |
| 15 | Peterhead | Bye | |
| 16 | Dumbarton | Berwick | 4 : 0 |
| 17 | East Fife | St Johnstone B | 2 : 1 |
| 18 | Bye | Dunfermline | |
| 19 | Kelty Hearts | Bye | |
| 20 | Elgin City | Banks O' Dee | 2 : 1 |
| 21 | Partick Thistle | Bye | |
| 22 | Bye | Alloa | |
| 23 | Arbroath | Bye | |
| 24 | Bye | Montrose | |
| 25 | Spartans | Bye | |
| 26 | Bye | Livingston | |
| 27 | Inverness | Bye | |
| 28 | Bye | Stirling | |
| 29 | Hamilton | Bye | |
| 30 | Dundee Utd B | Dundee FC B | 1 : 0 |
| 31 | Albion Rovers | Cowdenbeath | 3 : 4 |
| 32 | Bye | Morton |
1/16-finals
| 1 | Stranraer | Annan | 1 : 5 |
| 2 | Queen's Park | Edinburgh City | 1 : 0 |
| 3 | Rangers B | Fraserburgh | 5 : 0 |
| 4 | Stenhousemuir | Falkirk | 2 : 1 |
| 5 | Queen of South | Airdrieonians | 0 : 3 |
| 6 | East Kilbride | Cove Rangers | 3 : 2 |
| 7 | Ayr | Raith | 3 : 2 |
| 8 | Peterhead | Dumbarton | 1 : 0 |
| 9 | East Fife | Dunfermline | 0 : 2 |
| 10 | Kelty Hearts | Elgin City | 3 : 1 |
| 11 | Partick Thistle | Alloa | 1 : 3 |
| 12 | Arbroath | Montrose | 3 : 0 |
| 13 | Spartans | Livingston | 0 : 2 |
| 14 | Inverness | Stirling | 3 : 0 |
| 15 | Hamilton | Dundee Utd B | 4 : 0 |
| 16 | Cowdenbeath | Morton | 0 : 1 |
1/8-finals
| 1 | Annan | Queen's Park | 1 : 4 |
| 2 | Rangers B | Stenhousemuir | 4 : 1 |
| 3 | Airdrieonians | East Kilbride | 1 : 2 |
| 4 | Ayr | Peterhead | 2 : 1 |
| 5 | Dunfermline | Kelty Hearts | 2 : 1 |
| 6 | Alloa | Arbroath | 1 : 0 |
| 7 | Livingston | Inverness | 3 : 2 |
| 8 | Hamilton | Morton | 0 : 1 |
Quarter-finals
| 1 | Queen's Park | Rangers B | 3 : 1 |
| 2 | East Kilbride | Ayr | 3 : 2 |
| 3 | Dunfermline | Alloa | 1 : 0 |
| 4 | Livingston | Morton | 2 : 1 |
Semi-finals
| 1 | Queen's Park | East Kilbride | |
| 2 | Dunfermline | Livingston |
Final
| 1 | TBD #1 | TBD #2 |
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