| Cuarta Ronda | 19.01.2019 | Inverness CT | - | East Kilbride FC | 4:0 | ||||
| Octavos de final | 11.02.2019 | Ross County FC | - | Inverness CT | 2:2 |  |
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| Octavos de final | 19.02.2019 | Inverness CT | - | Ross County FC | 5:4 pn. | ||||
| Cuartos de final | 03.03.2019 | Dundee United | - | Inverness CT | 1:2 |
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