| 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 | 2 | 2 | 0 | 6 | 3 | +3 | 8 | XWWX | ||
| 2 | Dundee United | 4 | 2 | 1 | 1 | 6 | 4 | +2 | 8 | LWWX | ||
| 3 | East Fife | 4 | 2 | 1 | 1 | 5 | 3 | +2 | 8 | XWWL | ||
| 4 | Stenhousemuir | 4 | 1 | 0 | 3 | 4 | 6 | -2 | 3 | WLLL | ||
| 5 | Cowdenbeath | 4 | 1 | 0 | 3 | 2 | 7 | -5 | 3 | LLLW | ||
| Friday, 12 July 2019 | |||||
| 1 | Hearts | 1-1 | Dundee United | ||
| Saturday, 13 July 2019 | |||||
| 1 | Cowdenbeath | 2-0 | East Fife | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Cowdenbeath | 0-2 | Hearts | ||
| 2 | Stenhousemuir | 1-2 | Dundee United | ||
| Friday, 19 July 2019 | |||||
| 3 | Dundee United | 3-0 | Cowdenbeath | ||
| Saturday, 20 July 2019 | |||||
| 3 | East Fife | 2-0 | Stenhousemuir | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Dundee United | 0-2 | East Fife | ||
| Wednesday, 24 July 2019 | |||||
| 4 | Hearts | 2-1 | Stenhousemuir | ||
| Saturday, 27 July 2019 | |||||
| 5 | East Fife | 1-1 | Hearts | ||
| 5 | Stenhousemuir | 2-0 | Cowdenbeath | ||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 4 | 4 | 0 | 0 | 12 | 2 | +10 | 12 | WWWW | ||
| 2 | Forfar Athletic | 4 | 3 | 0 | 1 | 9 | 4 | +5 | 9 | WLWW | ||
| 3 | Montrose | 4 | 1 | 1 | 2 | 4 | 9 | -5 | 5 | XLWL | ||
| 4 | St.Johnstone | 4 | 1 | 0 | 3 | 6 | 5 | +1 | 3 | LWLL | ||
| 5 | Brechin City | 4 | 0 | 1 | 3 | 1 | 12 | -11 | 1 | XLLL | ||
| Saturday, 13 July 2019 | |||||
| 1 | Ross County | 4-1 | Montrose | ||
| 1 | Forfar Athletic | 3-0 | Brechin City | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Brechin City | 0-4 | Ross County | ||
| 2 | Montrose | 1-0 | St.Johnstone | ||
| Saturday, 20 July 2019 | |||||
| 3 | Montrose | 1-4 | Forfar Athletic | ||
| Sunday, 21 July 2019 | |||||
| 3 | St.Johnstone | 1-2 | Ross County | ||
| Wednesday, 24 July 2019 | |||||
| 4 | St.Johnstone | 4-0 | Brechin City | ||
| 4 | Ross County | 2-0 | Forfar Athletic | ||
| Saturday, 27 July 2019 | |||||
| 5 | Brechin City | 1-1 | Montrose | ||
| 5 | Forfar Athletic | 2-1 | St.Johnstone | ||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Hibernian | 4 | 3 | 1 | 0 | 8 | 1 | +7 | 11 | WWWX | ||
| 2 | Alloa Athletic | 4 | 2 | 1 | 1 | 8 | 8 | +0 | 7 | WWLX | ||
| 3 | Arbroath | 4 | 2 | 0 | 2 | 10 | 8 | +2 | 6 | LLWW | ||
| 4 | Elgin City | 4 | 1 | 1 | 2 | 7 | 7 | +0 | 5 | LWXL | ||
| 5 | Stirling Albion | 4 | 0 | 1 | 3 | 3 | 12 | -9 | 1 | LLLX | ||
| Saturday, 13 July 2019 | |||||
| 1 | Stirling Albion | 1-1 | Hibernian | ||
| 1 | Arbroath | 2-1 | Elgin City | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Alloa Athletic | 3-3 | Elgin City | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Stirling Albion | 1-6 | Arbroath | ||
| Saturday, 20 July 2019 | |||||
| 3 | Hibernian | 2-0 | Alloa Athletic | ||
| 3 | Elgin City | 3-0 | Stirling Albion | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Hibernian | 3-0 | Arbroath | ||
| 4 | Alloa Athletic | 2-1 | Stirling Albion | ||
| Friday, 26 July 2019 | |||||
| 5 | Elgin City | 0-2 | Hibernian | ||
| Saturday, 27 July 2019 | |||||
| 5 | Arbroath | 2-3 | Alloa Athletic | ||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 4 | 2 | 2 | 0 | 4 | 0 | +4 | 10 | WOOW | ||
| 2 | Inverness CT | 4 | 2 | 1 | 1 | 7 | 4 | +3 | 7 | LWWO | ||
| 3 | Peterhead | 4 | 1 | 2 | 1 | 3 | 4 | -1 | 6 | LOOW | ||
| 4 | Cove Rangers | 4 | 1 | 1 | 2 | 6 | 5 | +1 | 4 | WLOL | ||
| 5 | Raith Rovers | 4 | 1 | 0 | 3 | 4 | 11 | -7 | 3 | LWLL | ||
| Saturday, 13 July 2019 | |||||
| 1 | Raith Rovers | 0-3 | Dundee | ||
| 1 | Peterhead | 2-1 | Cove Rangers | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Peterhead | 0-0 | Inverness CT | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Cove Rangers | 0-0 | Dundee | ||
| Saturday, 20 July 2019 | |||||
| 3 | Dundee | 0-0 | Peterhead | ||
| 3 | Inverness CT | 4-1 | Raith Rovers | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Raith Rovers | 3-1 | Peterhead | ||
| 4 | Inverness CT | 3-2 | Cove Rangers | ||
| Saturday, 27 July 2019 | |||||
| 5 | Cove Rangers | 3-0 | Raith Rovers | ||
| Sunday, 28 July 2019 | |||||
| 5 | Dundee | 1-0 | Inverness CT | ||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 4 | 4 | 0 | 0 | 13 | 0 | +13 | 12 | WWWW | ||
| 2 | Morton | 4 | 2 | 1 | 1 | 14 | 8 | +6 | 8 | XWLW | ||
| 3 | Queen of the South | 4 | 1 | 2 | 1 | 10 | 10 | +0 | 6 | XWXL | ||
| 4 | Dumbarton | 4 | 1 | 0 | 3 | 3 | 12 | -9 | 3 | LLLW | ||
| 5 | Annan Athletic | 4 | 0 | 1 | 3 | 3 | 13 | -10 | 1 | LLXL | ||
| Saturday, 13 July 2019 | |||||
| 1 | Queen of the South | 0-3 | Motherwell | ||
| 1 | Annan Athletic | 0-1 | Dumbarton | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Morton | 6-1 | Dumbarton | ||
| 2 | Queen of the South | 3-3 | Annan Athletic | ||
| Friday, 19 July 2019 | |||||
| 3 | Motherwell | 4-0 | Morton | ||
| Saturday, 20 July 2019 | |||||
| 3 | Dumbarton | 1-4 | Queen of the South | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Dumbarton | 0-2 | Motherwell | ||
| 4 | Annan Athletic | 0-5 | Morton | ||
| Saturday, 27 July 2019 | |||||
| 5 | Motherwell | 4-0 | Annan Athletic | ||
| 5 | Morton | 3-3 | Queen of the South | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 4 | 3 | 1 | 0 | 8 | 5 | +3 | 10 | WXWW | ||
| 2 | Hamilton | 4 | 2 | 2 | 0 | 8 | 5 | +3 | 9 | WXWO | ||
| 3 | Airdrieonians | 4 | 1 | 1 | 2 | 7 | 8 | -1 | 5 | LXWL | ||
| 4 | Queen's Park | 4 | 0 | 3 | 1 | 4 | 5 | -1 | 5 | XXLO | ||
| 5 | Clyde | 4 | 0 | 1 | 3 | 6 | 10 | -4 | 1 | XLLL | ||
| Saturday, 13 July 2019 | |||||
| 1 | Partick Thistle | 1-0 | Airdrieonians | ||
| 1 | Hamilton | 0-0 | Queen's Park | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Queen's Park | 1-2 | Partick Thistle | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Clyde | 1-3 | Hamilton | ||
| Saturday, 20 July 2019 | |||||
| 3 | Hamilton | 2-2 | Partick Thistle | ||
| Sunday, 21 July 2019 | |||||
| 3 | Clyde | 2-3 | Airdrieonians | ||
| Wednesday, 24 July 2019 | |||||
| 4 | Airdrieonians | 2-2 | Queen's Park | ||
| 4 | Partick Thistle | 3-2 | Clyde | ||
| Saturday, 27 July 2019 | |||||
| 5 | Airdrieonians | 2-3 | Hamilton | ||
| Sunday, 28 July 2019 | |||||
| 5 | Queen's Park | 1-1 | Clyde | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 4 | 3 | 1 | 0 | 10 | 3 | +7 | 11 | WWWX | ||
| 2 | Ayr United | 4 | 2 | 1 | 1 | 12 | 5 | +7 | 7 | XWLW | ||
| 3 | Falkirk | 4 | 2 | 1 | 1 | 6 | 3 | +3 | 7 | WLWX | ||
| 4 | Stranraer | 4 | 1 | 1 | 2 | 9 | 5 | +4 | 5 | XLWL | ||
| 5 | Berwick Rangers | 4 | 0 | 0 | 4 | 0 | 21 | -21 | 0 | LLLL | ||
| Saturday, 13 July 2019 | |||||
| 1 | Falkirk | 1-1 | Livingston | ||
| 1 | Berwick Rangers | 0-7 | Ayr United | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Falkirk | 1-0 | Stranraer | ||
| 2 | Livingston | 2-1 | Ayr United | ||
| Saturday, 20 July 2019 | |||||
| 3 | Ayr United | 2-1 | Falkirk | ||
| 3 | Stranraer | 6-0 | Berwick Rangers | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Stranraer | 1-2 | Livingston | ||
| 4 | Berwick Rangers | 0-3 | Falkirk | ||
| Saturday, 27 July 2019 | |||||
| 5 | Ayr United | 2-2 | Stranraer | ||
| 5 | Livingston | 5-0 | Berwick Rangers | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dunfermline | 4 | 3 | 0 | 1 | 13 | 3 | +10 | 9 | WLWW | ||
| 2 | Albion Rovers | 4 | 2 | 1 | 1 | 3 | 7 | -4 | 7 | WOLW | ||
| 3 | St.Mirren | 4 | 1 | 2 | 1 | 3 | 3 | +0 | 6 | OOWL | ||
| 4 | East Kilbride | 4 | 1 | 1 | 2 | 1 | 5 | -4 | 5 | LWOL | ||
| 5 | FC Edinburgh | 4 | 1 | 0 | 3 | 2 | 4 | -2 | 3 | LLWL | ||
| Saturday, 13 July 2019 | |||||
| 1 | East Kilbride | 0-1 | Albion Rovers | ||
| Sunday, 14 July 2019 | |||||
| 1 | St.Mirren | 2-3 | Dunfermline | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Dunfermline | 6-0 | Albion Rovers | ||
| 2 | St.Mirren | 1-0 | FC Edinburgh | ||
| Saturday, 20 July 2019 | |||||
| 3 | FC Edinburgh | 1-0 | Dunfermline | ||
| 3 | East Kilbride | 0-0 | St.Mirren | ||
| Tuesday, 23 July 2019 | |||||
| 4 | Albion Rovers | 0-0 | St.Mirren | ||
| 4 | FC Edinburgh | 0-1 | East Kilbride | ||
| Saturday, 27 July 2019 | |||||
| 5 | Dunfermline | 4-0 | East Kilbride | ||
| 5 | Albion Rovers | 2-1 | FC Edinburgh | ||
| 5 | +5 | Kevin NISBET (Dunfermline) |
| 4 | +4 | Ross STEWART (Ross County) |
| +4 | Shane SUTHERLAND (Elgin City) | |
| +4 | Ross CUNNINGHAM (Hamilton, 2p) | |
| +4 | Billy McKAY (Ross County) | |
| +4 | Liam DONNELLY (Motherwell, 1p) | |
| 3 | +3 | Nicky CADDEN (Morton, 1p) |
| +3 | Luke McCOWAN (Ayr United) | |
| +3 | Ricky LAMIE (Livingston) | |
| +3 | Declan McMANUS (Falkirk) | |
| +3 | Michael MOFFAT (Ayr United) | |
| +3 | Craig HALKETT (Hearts) | |
| +3 | Shea GORDON (Partick Thistle) | |
| +3 | Alistair ROY (Airdrieonians, 1p) | |
| +3 | Liam BUCHANAN (Alloa Athletic) | |
| +3 | Alan TROUTEN (Alloa Athletic) | |
| +3 | James SCOTT (Motherwell) | |
| +3 | Michael TRAVIS (Forfar Athletic) |