| 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 | 4 | 4 | 0 | 0 | 8 | 0 | +8 | 12 | WWWW | ||
| 2 | Stirling Albion | 4 | 2 | 1 | 1 | 8 | 7 | +1 | 8 | WLXW | ||
| 3 | Inverness CT | 4 | 1 | 1 | 2 | 5 | 6 | -1 | 4 | LLXW | ||
| 4 | 1 | Cove Rangers | 4 | 1 | 0 | 3 | 6 | 10 | -4 | 3 | WLLL | |
| 5 | 1 | Peterhead | 4 | 1 | 0 | 3 | 4 | 8 | -4 | 3 | LWLL | |
| Saturday, 24 July 2021 | |||||
| 5 | Stirling Albion | 3-1 | Peterhead | ||
| 6 | McGregor | 7(p) | Brown | ||
| 12 | McNiff | ||||
| 47 | Leitch | ||||
| Sunday, 25 July 2021 | |||||
| 5 | Hearts | 1-0 | Inverness CT | ||
| 75 | Walker | ||||
| 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 | Arbroath | 4 | 3 | 0 | 1 | 6 | 3 | +3 | 9 | WLWW | |
| 3 | 1 | Kelty Hearts | 4 | 2 | 0 | 2 | 8 | 5 | +3 | 6 | LWWL | |
| 4 | 1 | Elgin City | 4 | 1 | 0 | 3 | 5 | 12 | -7 | 3 | WLLL | |
| 5 | 1 | East Fife | 4 | 0 | 0 | 4 | 2 | 9 | -7 | 0 | LLLL | |
| Saturday, 24 July 2021 | |||||
| 5 | East Fife | 2-3 | Elgin City | ||
| 2 | Smith | 15 | Mailer | ||
| 34(p) | McManus | 42 | Hester | ||
| 48 | Dingwall | ||||
| 5 | Arbroath | 3-2 | Kelty Hearts | ||
| 31 | Donnelly | 20 | Higginbotham | ||
| 52 | Hamilton | 27 | Cardle | ||
| 58(p) | Low | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 4 | 4 | 0 | 0 | 14 | 2 | +12 | 12 | WWWW | ||
| 2 | Forfar Athletic | 4 | 2 | 1 | 1 | 6 | 5 | +1 | 8 | LWOW | ||
| 3 | 1 | Ross County | 4 | 2 | 0 | 2 | 5 | 7 | -2 | 6 | WWLL | |
| 4 | 1 | Montrose | 4 | 1 | 1 | 2 | 4 | 6 | -2 | 4 | LLOW | |
| 5 | Brora Rangers | 4 | 0 | 0 | 4 | 0 | 9 | -9 | 0 | LLLL | ||
| Saturday, 24 July 2021 | |||||
| 5 | Dundee | 5-2 | Forfar Athletic | ||
| 12 | Adam | 62 | McCluskey | ||
| 31 | Panter | 81 | Anderson | ||
| 42 | Elliott | ||||
| 75(p) | Cummings | ||||
| 88 | Cummings | ||||
| 5 | Ross County | 4-1 | Montrose | ||
| 6 | Spittal | 61 | Johnston | ||
| 35 | Iacovitti | ||||
| 53 | White | ||||
| 56 | Spittal | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Raith Rovers | 4 | 2 | 2 | 0 | 5 | 0 | +5 | 9 | OOWW | ||
| 2 | 1 | Livingston | 4 | 2 | 1 | 1 | 7 | 3 | +4 | 8 | WOLW | |
| 3 | 1 | Cowdenbeath | 4 | 2 | 0 | 2 | 5 | 6 | -1 | 6 | LWWL | |
| 4 | Alloa Athletic | 4 | 1 | 1 | 2 | 2 | 3 | -1 | 4 | OLWL | ||
| 5 | Brechin City | 4 | 1 | 0 | 3 | 3 | 10 | -7 | 3 | WLLL | ||
| Saturday, 24 July 2021 | |||||
| 5 | Raith Rovers | 0-0 | Alloa Athletic | ||
| 5 | Livingston | 3-1 | Cowdenbeath | ||
| 21(og) | Todd | 9 | Buchanan | ||
| 38 | Anderson | ||||
| 53 | Sibbald | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ayr United | 4 | 3 | 1 | 0 | 7 | 0 | +7 | 10 | WWWO | ||
| 2 | 2 | Albion Rovers | 4 | 1 | 2 | 1 | 4 | 7 | -3 | 7 | WXLO | |
| 3 | 1 | Hamilton | 4 | 2 | 0 | 2 | 4 | 4 | +0 | 6 | LLWW | |
| 4 | 1 | FC Edinburgh | 4 | 1 | 1 | 2 | 4 | 5 | -1 | 4 | WXLL | |
| 5 | Falkirk | 4 | 1 | 0 | 3 | 6 | 9 | -3 | 3 | LLLW | ||
| 5 | Ayr United | 3-0 | Falkirk | ||
| Score awarded as 3-0. | |||||
| 5 | Hamilton | 1-2 | Albion Rovers | ||
| 79 | Smith | 37 | Wilson | ||
| 39 | Reilly | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Motherwell | 4 | 3 | 0 | 1 | 6 | 4 | +2 | 9 | WLWW | |
| 2 | 1 | Queen's Park | 4 | 2 | 1 | 1 | 3 | 2 | +1 | 7 | WOLW | |
| 3 | 1 | Queen of the South | 4 | 2 | 0 | 2 | 9 | 6 | +3 | 6 | WLWL | |
| 4 | 2 | Airdrieonians | 4 | 1 | 2 | 1 | 4 | 5 | -1 | 6 | LWOX | |
| 5 | Annan Athletic | 4 | 0 | 1 | 3 | 3 | 8 | -5 | 2 | LLLX | ||
| Saturday, 24 July 2021 | |||||
| 5 | Motherwell | 2-0 | Annan Athletic | ||
| 39 | Amaluzor | ||||
| 56 | Maguire | ||||
| 5 | Queen of the South | 4-1 | Airdrieonians | ||
| 23 | Roy | 90 | McGill | ||
| 35 | Roy | ||||
| 55 | Soares-Junior | ||||
| 58 | Roy | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Kilmarnock | 4 | 3 | 1 | 0 | 7 | 3 | +4 | 11 | WXWW | ||
| 2 | Stranraer | 4 | 2 | 0 | 2 | 5 | 3 | +2 | 6 | LWLW | ||
| 3 | 1 | Morton | 4 | 1 | 2 | 1 | 3 | 5 | -2 | 6 | WXOL | |
| 4 | 1 | Clyde | 4 | 1 | 1 | 2 | 5 | 6 | -1 | 5 | LXLW | |
| 5 | East Kilbride | 4 | 0 | 2 | 2 | 2 | 5 | -3 | 2 | XLOL | ||
| Saturday, 24 July 2021 | |||||
| 5 | Kilmarnock | 2-1 | Stranraer | ||
| 38 | Murray | 53 | Walker | ||
| 66 | Burke | ||||
| 5 | Morton | 2-1 | Clyde | ||
| 63 | Muirhead | 56 | Love | ||
| 68 | Muirhead | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | St.Mirren | 4 | 4 | 0 | 0 | 9 | 1 | +8 | 12 | WWWW | ||
| 2 | Dunfermline | 4 | 3 | 0 | 1 | 13 | 5 | +8 | 9 | WWLW | ||
| 3 | Partick Thistle | 4 | 2 | 0 | 2 | 6 | 7 | -1 | 6 | LWWL | ||
| 4 | Stenhousemuir | 4 | 1 | 0 | 3 | 5 | 10 | -5 | 3 | LLLW | ||
| 5 | Dumbarton | 4 | 0 | 0 | 4 | 2 | 12 | -10 | 0 | LLLL | ||
| Saturday, 24 July 2021 | |||||
| 5 | Dunfermline | 4-1 | Stenhousemuir | ||
| 15 | Wighton | 67 | Thomson | ||
| 36 | O'Hara | ||||
| 44 | Wighton | ||||
| 49 | O'Hara | ||||
| Sunday, 25 July 2021 | |||||
| 5 | St.Mirren | 2-0 | Partick Thistle | ||
| 25(p) | McGrath | ||||
| 90 | Shaughnessy | ||||
| 5 | +3 | Alistair ROY (Queen of the South) |
| 4 | Nathan AUSTIN (Kelty Hearts) | |
| Brian GRAHAM (Partick Thistle) | ||
| 3 | +2 | Kevin O'HARA (Dunfermline) |
| Nikolay TODOROV (Dunfermline) | ||
| Lawrence SHANKLAND (Dundee United) | ||
| Ruari PATON (Queen of the South) | ||
| +1 | Liam BUCHANAN (Cowdenbeath, 1p) | |
| +2 | Jason CUMMINGS (Dundee, 2p) | |
| +2 | Craig WIGHTON (Dunfermline) | |
| +1 | Luke DONNELLY (Arbroath) | |
| Liam BOYCE (Hearts) |