| Tue24 Sep2019 |
|  | 16:15 | Water Polo 1st | v Churcher's College | A |
|  | 17:00 | Basketball U15A, U14A | v City of London School | A |
| |
| Wed25 Sep2019 |
|  | 15:00 | Rugby Union U13A, U13B, U13D, U12A, U12B, U12D | v RGS, Guildford | H |
| |
| Thu26 Sep2019 |
|  | 14:00 | Rackets 1st | v Wellington College | H |
|  | 14:30 | Squash U18A, U18B | v Eton College | H |
| |
| Fri27 Sep2019 |
| | 14:45 | Rugby Union U11A, U11B, U11D, U11F | v Donhead, Wimbledon College Preparatory | A |
| |
| Sat28 Sep2019 |
| | 10:00 | Rugby Union U12A, U12B, U12C, U12D, U12E, U12F | v Dulwich College | A |
| | 10:00 | Rugby Union U13A, U13B, U13C, U13D, U13E | v Dulwich College | H |
| | 14:30 | Rugby Union 2nd XV, 3rd XV, 4th XV, 5th XV, U15A, U15B, U15C | v Radley College | A |
| | 14:30 | Rugby Union U16A, U16B, U16C, U16D, U14A, U14B, U14C, U14D, U14E, U14F, U14G | v Radley College | H |
| | 15:00 | Rugby Union 1st XV | v Radley College | A |
| |
| Sun29 Sep2019 |
| | 12:00 | FENCING MATCH VERSUS ABINGDON | ST. PAUL'S |
|  | 12:00 | Fencing FOIL A, EPEE A | v Abingdon School | H |
| |
| Tue1 Oct2019 |
| | 14:30 | Rugby Union U10A, U10B, U10C, U10D, U10E | v Donhead, Wimbledon College Preparatory | H |
| |
| Wed2 Oct2019 |
| | 14:30 | Rugby Union U12A, U12B, U12C, U12D | v Dragon School | A |
| | 14:30 | Rugby Union U13A, U13B, U13C, U13D | v Dragon School | H |
| |
| Thu3 Oct2019 |
|  | 15:30 | Swimming 1st | v Cranleigh School | H |
| | 19:00 | Squash U18A | v Roehampton Club | A |
| |
| Fri4 Oct2019 |
| | 14:30 | Rugby Union U10A, U10C, U10E | v St Benedict's School | H |
| | 15:00 | Rugby Union U11A, U11C, U11E | v St Benedict's School | A |
| |
| Sat5 Oct2019 |
| | 14:30 | Rugby Union 1st XV, 2nd XV, 3rd XV, 4th XV, 5th XV, U14A, U14B, U14C, U14D, U14E, U14F | v Harrow School | A |
| | 14:30 | Rugby Union U16A, U16B, U16C, U16D, U15A, U15B, U15C | v Harrow School | H |
| |
| Sun6 Oct2019 |
| | 11:00 | Rugby Union U11A | v New Hall School | A |
| |
| Tue8 Oct2019 |
| | 14:30 | Squash U16A | v Epsom College | A |
| | 14:30 | Squash U16A | v Reed's School | A |
| | 16:00 | Water Polo U16A | v The Haberdashers' Aske's Boys' School | A |
| | 17:00 | Basketball 1st | v City of London School | H |
| |
| Wed9 Oct2019 |
| | 14:30 | Rugby Union U13A, U13B, U13C, U13D | v Caldicott Preparatory School | A |
| | 14:30 | Rugby Union U12A, U12B, U12C, U12D | v Caldicott Preparatory School | H |
| |
| Thu10 Oct2019 |
| | 15:00 | Squash U18A, U18B, U15A | v Charterhouse | H |
| | 17:45 | Basketball 1st | v Whitgift School | H |
| |
| Fri11 Oct2019 |
| | 14:30 | Rugby Union U12A, U12B, U12C, U12D, U12E, U12F | v London Oratory School | H |
| | 15:00 | Rugby Union U11A, U11B | v Emanuel School | A |
