| ROUND | R1 | R2 | QF | SF | F | ||||
| r1 | r2 | r3 | r4 | r5 | |||||
| Season archive |
| Group A | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Hearts | 3 | 3 | 0 | 0 | 7 | 0 | +7 | 9 | WWW- | ||
| 2 | Stirling Albion | 3 | 1 | 1 | 1 | 5 | 6 | -1 | 5 | LXW- | ||
| 3 | Inverness CT | 3 | 1 | 1 | 1 | 5 | 5 | +0 | 4 | LXW- | ||
| 4 | Peterhead | 3 | 1 | 0 | 2 | 3 | 5 | -2 | 3 | WLL- | ||
| 5 | Cove Rangers | 4 | 1 | 0 | 3 | 6 | 10 | -4 | 3 | WLLL | ||
| Tuesday, 20 July 2021 | |||||
| 4 | Stirling Albion | 0-2 | Hearts | ||
| 31 | Boyce | ||||
| 74 | Pollock | ||||
| 4 | Cove Rangers | 3-1 | Inverness CT | ||
| 35 | McIntosh | 90(p) | Duku | ||
| 38 | Megginson | ||||
| 85 | Yule | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee United | 4 | 4 | 0 | 0 | 9 | 1 | +8 | 12 | WWWW | ||
| 2 | 1 | Kelty Hearts | 3 | 2 | 0 | 1 | 6 | 2 | +4 | 6 | WWL- | |
| 3 | 1 | Arbroath | 3 | 2 | 0 | 1 | 3 | 1 | +2 | 6 | LWW- | |
| 4 | East Fife | 3 | 0 | 0 | 3 | 0 | 6 | -6 | 0 | LLL- | ||
| 5 | Elgin City | 3 | 0 | 0 | 3 | 2 | 10 | -8 | 0 | LLL- | ||
| Tuesday, 20 July 2021 | |||||
| 4 | East Fife | 0-1 | Dundee United | ||
| 40 | Pawlett | ||||
| 4 | Elgin City | 1-3 | Kelty Hearts | ||
| 5 | Little | 52 | Russell | ||
| 76 | Austin | ||||
| 87 | Austin | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dundee | 3 | 3 | 0 | 0 | 9 | 0 | +9 | 9 | WWW- | |
| 2 | 1 | Forfar Athletic | 3 | 2 | 1 | 0 | 4 | 0 | +4 | 8 | WOW- | |
| 3 | Montrose | 3 | 1 | 1 | 1 | 3 | 2 | +1 | 4 | LOW- | ||
| 4 | Ross County | 3 | 1 | 0 | 2 | 1 | 6 | -5 | 3 | WLL- | ||
| 5 | Brora Rangers | 4 | 0 | 0 | 4 | 0 | 9 | -9 | 0 | LLLL | ||
| Wednesday, 21 July 2021 | |||||
| 4 | Montrose | 0-2 | Dundee | ||
| 70(p) | Cummings | ||||
| 73 | McCowan | ||||
| 4 | Brora Rangers | 0-1 | Ross County | ||
| 53 | Iacovitti | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Raith Rovers | 3 | 2 | 1 | 0 | 5 | 0 | +5 | 7 | OWW- | ||
| 2 | Cowdenbeath | 3 | 2 | 0 | 1 | 4 | 3 | +1 | 6 | WWL- | ||
| 3 | Livingston | 3 | 1 | 1 | 1 | 4 | 2 | +2 | 5 | OLW- | ||
| 4 | Alloa Athletic | 3 | 1 | 0 | 2 | 2 | 3 | -1 | 3 | LWL- | ||
| 5 | Brechin City | 4 | 1 | 0 | 3 | 3 | 10 | -7 | 3 | WLLL | ||
| Tuesday, 20 July 2021 | |||||
| 4 | Brechin City | 1-0 | Alloa Athletic | ||
| 55 | Scott | ||||
| Wednesday, 21 July 2021 | |||||
| 4 | Livingston | 0-0 | Raith Rovers | ||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Ayr United | 3 | 2 | 1 | 0 | 4 | 0 | +4 | 7 | WWO- | |
| 2 | 1 | Hamilton | 3 | 2 | 0 | 1 | 3 | 2 | +1 | 6 | LWW- | |
| 3 | 2 | FC Edinburgh | 4 | 1 | 1 | 2 | 4 | 5 | -1 | 4 | WXLL | |
| 4 | 1 | Albion Rovers | 3 | 0 | 2 | 1 | 2 | 6 | -4 | 4 | XLO- | |
| 5 | 1 | Falkirk | 3 | 1 | 0 | 2 | 6 | 6 | +0 | 3 | LLW- | |
| Tuesday, 20 July 2021 | |||||
| 4 | Hamilton | 0-1 | Ayr United | ||
| 27 | Salkeld | ||||
| 4 | FC Edinburgh | 3-0 | Falkirk | ||
| Score awarded as 3-0. | |||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Queen's Park | 4 | 2 | 1 | 1 | 3 | 2 | +1 | 7 | WOLW | |
| 2 | 2 | Airdrieonians | 3 | 1 | 2 | 0 | 3 | 1 | +2 | 6 | WOX- | |
| 3 | 2 | Motherwell | 3 | 2 | 0 | 1 | 4 | 4 | +0 | 6 | LWW- | |
| 4 | 1 | Queen of the South | 3 | 1 | 0 | 2 | 5 | 5 | +0 | 3 | LWL- | |
| 5 | Annan Athletic | 3 | 0 | 1 | 2 | 3 | 6 | -3 | 2 | LLX- | ||
| Tuesday, 20 July 2021 | |||||
| 4 | Annan Athletic | 1-2 | Queen's Park | ||
| 22(og) | McHugh | 13(og) | Swinglehurst | ||
| 81 | Murray | ||||
| Wednesday, 21 July 2021 | |||||
| 4 | Airdrieonians | 2-0 | Motherwell | ||
| 66 | McCabe | ||||
| 79 | McGill | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Kilmarnock | 3 | 2 | 1 | 0 | 5 | 2 | +3 | 8 | XWW- | |
| 2 | 1 | Stranraer | 3 | 2 | 0 | 1 | 4 | 1 | +3 | 6 | WLW- | |
| 3 | Clyde | 3 | 1 | 1 | 1 | 4 | 4 | +0 | 5 | XLW- | ||
| 4 | Morton | 3 | 0 | 2 | 1 | 1 | 4 | -3 | 3 | XOL- | ||
| 5 | East Kilbride | 4 | 0 | 2 | 2 | 2 | 5 | -3 | 2 | XLOL | ||
| Tuesday, 20 July 2021 | |||||
| 4 | Kilmarnock | 1-1 | Morton | ||
| 90 | Connell | 16 | McGregor | ||
| 4 | East Kilbride | 2-2 | Clyde | ||
| 4 | Erskine | 11 | Jones | ||
| 30 | Victoria | 26 | Goodwillie | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | St.Mirren | 3 | 3 | 0 | 0 | 7 | 1 | +6 | 9 | WWW- | |
| 2 | 1 | Dunfermline | 3 | 2 | 0 | 1 | 9 | 4 | +5 | 6 | WLW- | |
| 3 | 1 | Partick Thistle | 3 | 2 | 0 | 1 | 6 | 5 | +1 | 6 | WWL- | |
| 4 | 1 | Stenhousemuir | 3 | 1 | 0 | 2 | 4 | 6 | -2 | 3 | LLW- | |
| 5 | Dumbarton | 4 | 0 | 0 | 4 | 2 | 12 | -10 | 0 | LLLL | ||
| Tuesday, 20 July 2021 | |||||
| 4 | Partick Thistle | 2-0 | Dumbarton | ||
| 45 | Graham | ||||
| 52 | Graham | ||||
| 4 | Stenhousemuir | 1-3 | St.Mirren | ||
| 76 | Orr | 50 | Main | ||
| 66 | Dennis | ||||
| 90 | Erwin | ||||
| 4 | +2 | Nathan AUSTIN (Kelty Hearts) |
| +2 | Brian GRAHAM (Partick Thistle) | |
| 3 | Nikolay TODOROV (Dunfermline) | |
| Lawrence SHANKLAND (Dundee United) | ||
| Ruari PATON (Queen of the South) | ||
| +1 | Liam BOYCE (Hearts) | |
| 2 | +1 | David GOODWILLIE (Clyde, 1p) |
| Lewis VAUGHAN (Raith Rovers) | ||
| Ross MacLEAN (Dumbarton) | ||
| +1 | Peter PAWLETT (Dundee United) | |
| Brad SPENCER (Raith Rovers) | ||
| Nathan FLANAGAN (Stirling Albion) | ||
| Gary MACKAY-STEVEN (Hearts) | ||
| Zak RUDDEN (Partick Thistle) | ||
| +1 | Mitchel MEGGINSON (Cove Rangers) | |
| Kris RENTON (Cowdenbeath) | ||
| Alistair ROY (Queen of the South) | ||
| Liam BUCHANAN (Cowdenbeath, 1p) | ||
| +1 | Thomas ORR (Stenhousemuir, 1p) | |
| Callumn MORRISON (Falkirk) | ||
| +1 | Manny DUKU (Inverness CT, 1p) | |
| Tomi ADELOYE (Ayr United) | ||
| Paul McMULLAN (Dundee) | ||
| Fraser FYVIE (Cove Rangers) | ||
| Luke DONNELLY (Arbroath) | ||
| +1 | Curtis MAIN (St.Mirren) |