| 4. Round | 20/01/2019 | Heart of Midlothian | - | Livingston FC | 1:0 |  |
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| Round of 16 | 10/02/2019 | Heart of Midlothian | - | Auchinleck Talbot | 4:0 | ||||
| Quarter-finals | 04/03/2019 | Partick Thistle | - | Heart of Midlothian | 1:1 | ||||
| Quarter-finals | 12/03/2019 | Heart of Midlothian | - | Partick Thistle | 2:1 | |
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| Semi-finals | 13/04/2019 | Heart of Midlothian | - | Inverness CT | 3:0 | |
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| Final | 25/05/2019 | Heart of Midlothian | - | Celtic FC | 1:2 |
England