| Sat31 Aug2019 |
|  | 10:00 | Rugby Union 1st XV | v Bedford School | H |
| | 10:00 | Rugby Union 1st XV | v The Perse School | H |
| | 10:00 | Rugby Union 1st XV | v Preseason Tournament | H |
| | 10:45 | Rugby Union 1st XV | v New Hall School | H |
| | 11:30 | Rugby Union U14A | v Bedford Modern School | A |
| | 11:30 | Rugby Union U15A | v New Hall School | H |
| |
| Sun1 Sep2019 |
| | 10:00 | Rugby Union U15A | v Pre-season Festival | H |
| |
| Sat7 Sep2019 |
| | 09:30 | Rugby Union U12 Gold, U12 Blue, U12 Red | v Training | H |
| | 10:30 | Rugby Union U15A, U15B, U15C, U13 Gold, U13 Blue, U13 Red | v Brentwood School | A |
| | 10:30 | Rugby Union 2nd XV, U16B, U16C, U14A, U14B, U14C, U14D | v Brentwood School | H |
| | 10:30 | Rugby Union 3rd XV, U16A | v Training | H |
|  | 13:30 | Netball 1st VII | v OA Netball Team | H |
| | 14:00 | Rugby Union 1st XV | v Bishop's Stortford High School | H |
| |
| Mon9 Sep2019 |
|  | 16:30 | Basketball U15A | v tbc | tbc |
| |
| Fri13 Sep2019 |
|  | 19:00 | Swimming Senior Boys, Inters, Juniors | v ESSA National Relays @ Woodside Leisure Centre | A |
| |
| Sat14 Sep2019 |
| | 11:00 | Rugby Union U16A, U16B, U14A, U14B, U14C | v Bedford Modern School | A |
| | 11:00 | Rugby Union U15A, U15B, U13 Gold, U13 Blue, U13 Red, U12 Gold, U12 Blue, U12 Red | v Bedford Modern School | H |
| | 14:00 | Rugby Union 1st XV, 2nd XV | v Bedford Modern School | A |
| | 14:30 | Rugby Union 3rd XV | v The Oratory School | A |
| | 14:30 | Rugby Union 4th XV | v Oundle School | H |
| |
| Sun15 Sep2019 |
|  | 09:00 | Skiing Seniors | v ESSKIA Qualifying Race | A |
| |
| Mon16 Sep2019 |
| | 16:30 | Basketball U15A | v tbc | tbc |
| |
| Tue17 Sep2019 |
| | 16:15 | Netball 1st VII | v Chancellor's School | H |
| |
| Wed18 Sep2019 |
|  | 14:30 | Football 1st XI | v Sandringham School | H |
| | 15:00 | Netball 1st VII | v Roundwood Park School | tbc |
| |
| Thu19 Sep2019 |
| | 17:30 | Rugby Union 1st XV, U16A | v St Albans College, Buenos Aires | H |
| |
| Sat21 Sep2019 |
|  | 09:00 | Lacrosse 1st | v Berkhamsted School | A |
| | 10:30 | Rugby Union U13 Gold, U13 Blue | v St John's Beaumont School | A |
| | 10:30 | Rugby Union U12 Gold, U12 Blue | v St John's Beaumont School | H |
| | 14:45 | Rugby Union U15A, U15B, U14A, U14B | v Bloxham School | A |
| | 14:45 | Rugby Union 1st XV, 2nd XV, 3rd XV, U16A, U16B | v Bloxham School | H |
| |
| Mon23 Sep2019 |
| | 16:30 | Basketball U15A | v tbc | tbc |
| |
| Tue24 Sep2019 |
|  | 14:00 | Golf Mixed U18A | v Haileybury | A |
| | 14:30 | Rugby Union U14A, U14B, U14C, U14D | v Watford Grammar School for Boys | H |
| | 17:00 | Netball 1st VII | v St Helen's School | H |
