| Sat24 Apr2021 |
|  | 11:30 | Cricket U18A | v Uppingham School | A |
|  | 11:30 | Athletics | Rugby | Rugby School |
|  | 14:00 | Badminton Mixed U18A, U18A, U18B | v Uppingham School | H |
| | 14:00 | Badminton Mixed U18A, U18A, U18B | v Uppingham School | H |
| | 14:15 | Cricket U18A, U18C, U15A, U15A, U15B | v Uppingham School | A |
| | 14:15 | Cricket U18B, U18D, U14A, U14B | v Uppingham School | H |
|  | 14:30 | Tennis U18A, U18B, U18C, U16A, U15A, U15B, U15C, U14A, U14B, U14C | v Uppingham School | A |
| | 14:30 | Tennis U18A, U18B, U18C, U16A, U15A, U15B, U14A, U14B | v Uppingham School | H |
| |
| Wed28 Apr2021 |
| | 14:00 | Cricket U13A, U13B, U13C, U13D | v Oakham School | A |
|  | 14:30 | Cricket Sixes U13A, U13A, U13B, U12A, U12A, U12B | v Oakham School | tbc |
| | 14:30 | Tennis U13A, U13B, U13C, U12A, U12B, U12C | v Oakham School | A |
| | 14:30 | Tennis U13A, U12A | v Oakham School | H |
| |
| Sat1 May2021 |
| | 11:30 | Cricket U18A, U18A | v Oakham School | H |
| | 11:30 | Athletics | Bromsgrove | Bromsgrove School |
| | 14:00 | Tennis U15A, U15B, U14A, U14B | v Haileybury | A |
| | 14:00 | Tennis U18B, U18C, U18D | v Haileybury | H |
| | 14:15 | Cricket U18B, U18D, U14A, U14A, U14B, U14C | v Oakham School | A |
| | 14:15 | Cricket U18A, U18C, U15A, U15A, U15B, U15C | v Oakham School | H |
| | 14:15 | Tennis U18A, U18B, U18C, U18D, U16A, U15A, U15B, U15C, U15D | v Oakham School | A |
| | 14:15 | Tennis U18A, U18B, U18C, U18D, U15A, U14A, U14A, U14B, U14C, U14D | v Oakham School | H |
| | 14:30 | Cricket U18E, U14D | v Oakham School | A |
| | 14:30 | Tennis U15B, U14B | v Oakham School | A |
| |
| Mon3 May2021 |
| | 14:30 | Cricket U12A, U12B, U12C, U12D | v Stamford | A |
| | 14:30 | Cricket U12A, U12B, U12C, U12D | v Stamford | H |
| | 14:30 | Tennis U12A, U12B, U12C, U12D | v Stamford | H |
| | 14:30 | Tennis U12A, U12B | v Stamford | tbc |
| | 16:00 | Tennis U13A, U13B, U13C, U13D | v Stamford | A |
| |
| Tue4 May2021 |
|  | 18:00 | Hockey Boys 1st Xl | v Stamford | H |
| |
| Wed5 May2021 |
| | 14:30 | Cricket U13A, U13B, U13C, U13D | v Stamford | A |
| | 14:30 | Cricket Sixes U13A, U13B, U13C, U12A, U12B | v Stamford | tbc |
| | 14:30 | Tennis U13A, U13B | v Stamford | tbc |
| |
| Thu6 May2021 |
| | 14:15 | Athletics | Oakham Relays | Oakham School |
|  | 14:30 | Golf 6th | v Schools' Quadrangluar | A |
| |
| Fri7 May2021 |
| | 18:00 | Hockey Girls 1s | v Stamford | H |
| | tbc | Hockey Boys 1st Xl, Girls 1s | v Stamford | H |
| |
| Sat8 May2021 |
| | 11:30 | Cricket U18A | v Stamford | A |
| | 14:15 | Cricket U18A, U14A, U14B, U14C, U14D | v Stamford | A |
| | 14:15 | Cricket U18B, U18C, U18D, U15A, U15A, U15B, U15C, U14A | v Stamford | H |
| | 14:30 | Tennis U18A, U18B, U18C, U18C, U16A, U16B, U15A, U15B, U14A, U14B | v Stamford | A |
| | 14:30 | Tennis U18A, U18B, U16A, U16B, U15A, U15B, U15C, U14A, U14B, U14C | v Stamford | H |
| |
| Wed12 May2021 |
| | 14:30 | Cricket U13A, U13B | v Witham Hall School | A |
| | 14:30 | Cricket U13A, U13B, U13C | v Witham Hall School | H |
| | 14:30 | Cricket Sixes U13A, U13B, U13C | v Witham Hall School | tbc |
| | 14:30 | Tennis U13A, U12A | v Witham Hall School | tbc |
| |
| Thu13 May2021 |
|  | 14:30 | Netball 1st VII | v Uppingham School | H |
| |
| Fri14 May2021 |
| | 16:30 | Tennis U13A, U13A, U13B, U13B, U12A, U12A, U12B, U12B | v Witham Hall School | tbc |
| |
| Sat15 May2021 |
| | | Athletics | Oundle | Oundle School, Northamptonshire, PE8 4GH |
| | 11:30 | Cricket U18A | v Uppingham School | H |
| | 14:00 | Badminton Mixed U18A, U18B | v Uppingham School | A |
| | 14:15 | Cricket U18B, U18D, U14A, U14B | v Uppingham School | A |
| | 14:15 | Cricket U18A, U18C, U15A, U15A, U15B | v Uppingham School | H |
| | 14:30 | Athletics Mixed U18A, U16A, U15A, U14A | v Stamford | H |
| | 14:30 | Tennis U18A, U18B, U18C, U16A, U15A, U15B, U14A, U14B | v Uppingham School | A |
| | 14:30 | Tennis U18A, U18B, U18C, U16A, U15A, U15B, U15C, U14A, U14B, U14C | v Uppingham School | H |
