| Match Date | Competition | Home | | v | | | | | Away |
| 13/09/20 10:30 | Premiership | Stillington Royal F.C | 1 | | 8 |
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| F.C Borowalkers Charity Team |
| 27/09/20 10:30 | Premiership | Yarm Athletic F.C | 1 | | 3 |
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| F.C Borowalkers Charity Team |
| 04/10/20 10:30 | Premiership | Portrack F.C | 3 | | 2 |
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| F.C Borowalkers Charity Team |
| 11/10/20 10:30 | North Riding Sunday County Cup | F.C Borowalkers Charity Team | 8 | | 0 |
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| Cleveland Lions F.C |
| 18/10/20 10:30 | Premiership | Village Park Rangers F.C | 1 | | 4 |
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| F.C Borowalkers Charity Team |
| 01/11/20 10:30 | Premiership | F.C Borowalkers Charity Team | 5 | | 1 |
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| Village Park Rangers F.C |
| 06/12/20 10:30 | Premiership | F.C Borowalkers Charity Team | 4 | | 4 |
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| Yarm Athletic F.C |
| 20/12/20 10:30 | North Riding Sunday County Cup | Middlesbrough Dormans F.C | 4 | | 1 |
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| F.C Borowalkers Charity Team |