| Tue17 Sep2019 |
|  | 13:45 | Rugby Union U14A | v St Joseph's College | H |
| |
| Wed18 Sep2019 |
| | 14:30 | Rugby Union 1st XV | v Esher College | H |
| | 14:30 | Rugby Union U14A | v Raynes Park High School | H |
|  | 15:30 | Football U12A | v Southborough School | A |
| |
| Thu19 Sep2019 |
| | 15:30 | Football U15A | v Southborough School | tbc |
| |
| Fri20 Sep2019 |
| | 14:00 | Rugby Union U12A | v Saint Cecilia's Church of England School | H |
| |
| Mon23 Sep2019 |
| | 14:30 | Rugby Union U13A | v Saint Cecilia's Church of England School | A |
| | tbc | Football | v Hollyfield School & 6th Form Centre | A |
| |
| Tue24 Sep2019 |
| | 14:30 | Rugby Union U14A | v Saint Cecilia's Church of England School | H |
| |
| Wed25 Sep2019 |
| | 14:30 | Rugby Union 1st XV | v Saint Cecilia's Church of England School | H |
| | tbc | Football U14A | v Southborough School | tbc |
| |
| Thu26 Sep2019 |
| | 14:30 | Rugby Union U16A, U15A | v Saint Cecilia's Church of England School | A |
| | 15:30 | Rugby Union U15A | v Southborough School | H |
| | tbc | Football | v Hollyfield School & 6th Form Centre | H |
| |
| Mon30 Sep2019 |
| | 14:30 | Rugby Union U16A | v Bishop Thomas Grant School | H |
| | tbc | Football | v Hollyfield School & 6th Form Centre | H |
| |
| Tue1 Oct2019 |
| | 14:30 | Rugby Union U14A | v Bishop Thomas Grant School | A |
| |
| Wed2 Oct2019 |
| | 14:30 | Rugby Union U15A | v Glyn School | A |
| | tbc | Football U12A | v Harris Academy Wimbledon | H |
| |
| Thu3 Oct2019 |
| | 14:30 | Rugby Union U13A | v Bishop Thomas Grant School | A |
| | 15:30 | Rugby Union U12A | v Southborough School | A |
| |
| Mon7 Oct2019 |
| | 14:00 | Football U13A | v Ibstock Place School | A |
|  | 14:15 | Badminton U15A | v Kings College Wimbledon | A |
| |
| Tue8 Oct2019 |
| | 14:00 | Football U12A, U12B | v Ibstock Place School | tbc |
| |
| Wed9 Oct2019 |
| | 14:30 | Rugby Union U13B, U13C | v Christ's Hospital | A |
| | 14:30 | Rugby Union U15A | v St James Senior Boys' School | H |
| |
| Thu10 Oct2019 |
| | 14:00 | Football U15A | v Ibstock Place School | H |
| | 15:30 | Rugby Union U16A | v Southborough School | H |
| | 15:30 | Rugby Union U13A | v ARK Putney Academy | A |
| | tbc | Rugby Union U13A | v St James Senior Boys' School | A |
| |
| Fri11 Oct2019 |
| | 14:00 | Football U14A | v Ibstock Place School | H |
| | 15:30 | Rugby Union U12A | v Bishop Thomas Grant School | H |
| |
| Mon14 Oct2019 |
| | 15:00 | Football | v Hollyfield School & 6th Form Centre | A |
| |
| Tue15 Oct2019 |
| | 15:30 | Football U13A | v Harris Academy Merton | A |
| | 16:00 | Rugby Union U14A | v Woodcote High School | A |
| |
| Wed16 Oct2019 |
| | 14:30 | Football U16A | v Haberdashers' Aske's Knights Academy | H |
| | 14:30 | Rugby Union 1st XV | v Christ's Hospital | A |
