| Fri17 Sep2021 |
|  | 14:30 | Football U11A, U11B, U11C, U11D, U11E | v King's Rochester | H |
| |
| Tue21 Sep2021 |
| | 15:15 | Football U15A, U14A | v Kent College | A |
| | 15:15 | Football U15A, U14A | v Kent College | A |
| | 15:15 | Football U15B | v Kent College | H |
|  | 16:30 | Hockey 1st XI | v Kent College Pembury | H |
| |
| Wed22 Sep2021 |
| | 14:00 | Football U11A, U11B, U11C, U11D | v St. Lawrence | H |
|  | 14:00 | Hockey Sevens U11A, U11B | v Northbourne Park School | A |
| | 14:00 | Hockey Sevens U13A, U13B | v Wellesley House | H |
| |
| Thu23 Sep2021 |
| | 15:15 | Football 1st XI | v Kent College | H |
| |
| Fri24 Sep2021 |
| | 15:00 | Football U11A | v Junior King's School | H |
| |
| Sat25 Sep2021 |
| | tbc | Football 1st XI | v Old Edmundians | H |
| |
| Mon27 Sep2021 |
| | 14:30 | Football U13B | v King's Rochester | A |
| | 14:30 | Football U13A, U13C, U13D | v King's Rochester | H |
| |
| Tue28 Sep2021 |
| | 14:30 | Football U15A, U15B | v The Archbishop's School | tbc |
| | 15:00 | Hockey Girls U15B | v King's Rochester | A |
| | 15:00 | Hockey Girls U15A | v King's Rochester | H |
| |
| Wed29 Sep2021 |
| | 14:00 | Football U13A | v Shapira Cup | A |
| | 14:00 | Hockey Girls U13A, U13B, U13C, U13D, U11A, U11B, U11C, U11D | v Junior King's School | tbc |
| | 14:00 | Hockey Sevens U13A, U13B, U13C, U13D | v Junior King's School | A |
| | 14:00 | Hockey Sevens U11A, U11B, U11C | v Junior King's School | H |
| |
| Thu30 Sep2021 |
| | 15:00 | Hockey 2nd XI | v King's Rochester | A |
| | 15:00 | Hockey 1st XI | v King's Rochester | H |
| |
| Fri1 Oct2021 |
| | 14:30 | Football U11A | v Dover College | H |
| |
| Tue5 Oct2021 |
| | 14:30 | Football U15A | v The Abbey School | tbc |
| | 15:00 | Hockey Girls U15B | v Ashford School | A |
| | 15:00 | Hockey Girls U15A | v Ashford School | H |
| |
| Wed6 Oct2021 |
| | 14:00 | Football U13A, U13B, U13C | v Junior King's School | A |
| | 14:00 | Football U11A, U11B | v Northbourne Park School | H |
| | 14:00 | Hockey Girls U13A, U13B, U12A, U12B | v Duke of York's Royal Military School | H |
| | 14:00 | Hockey Sevens U13A, U13B, U13C, U13D | v Duke of York's Royal Military School | H |
| | 14:00 | Hockey Sevens U11A, U11B, U11C | v St Lawrence College Junior School | A |
| |
| Thu7 Oct2021 |
| | 15:00 | Hockey 1st XI | v Ashford School | A |
| | 15:00 | Hockey 2nd XI | v Ashford School | H |
| |
| Fri8 Oct2021 |
| | 14:30 | Football U11A | v Dover College | A |
| |
| Tue12 Oct2021 |
| | 14:30 | Football U15A | v tbc Knock Out Round | tbc |
| | 14:30 | Football U15A, U15B | v Dover College | A |
| | 14:30 | Hockey Girls U15B | v Dover College | A |
| |
| Wed13 Oct2021 |
| | 14:00 | Football U11A, U11B | v Lorendon | A |
| | 14:00 | Hockey Sevens U11A, U11B, U11C | v King's Rochester | A |
| | 14:00 | Hockey Sevens U13A, U13B | v Northbourne Park School | A |
| |
| Thu14 Oct2021 |
| | 14:30 | Football 1st XI | v Dover College | H |
| | 14:30 | Hockey 2nd XI | v Dover College | H |
| | 15:00 | Hockey 1st XI | v Langley Park School for Boys | A |
| |
| Fri15 Oct2021 |
| | 14:00 | Football U9A, U9B | v King's Rochester | H |
