| I-League | 08.12.19 | Mohun Bagan FC | - | Churchill Brothers | 2:4 |  |
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| I-League | 22.02.20 | Churchill Brothers | - | Mohun Bagan FC | 0:3 | ||||
| I-League | 19.01.21 | Punjab FC | - | Churchill Brothers | 0:1 | ||||
| I-League | 27.03.21 | Churchill Brothers | - | Punjab FC | 3:2 |  |
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| I-League | 04.03.22 | Punjab FC | - | Churchill Brothers | 2:2 | ||||
| I-League | 03.05.22 | Churchill Brothers | - | Punjab FC | 2:1 | ||||
| I-League | 15.11.22 | Churchill Brothers | - | Rajasthan United | 1:2 | |
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| I-League | 17.01.23 | Rajasthan United | - | Churchill Brothers | 0:5 | ||||
| Super Cup | 19.04.23 | NorthEast United FC | - | Churchill Brothers | 6:3 | ||||
| I-League | 01.12.23 | Delhi FC | - | Churchill Brothers | 2:1 |
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