| Tue7 Apr2020 |
|  | 10:00 | Cricket 1st XI, 2nd XI | v U18 Eastbourne Festival | A |
| |
| Wed8 Apr2020 |
| | 10:00 | Cricket 1st XI, 2nd XI | v U18 Eastbourne Festival | A |
| |
| Thu9 Apr2020 |
| | 10:00 | Cricket 1st XI, 2nd XI | v U18 Eastbourne Festival | A |
| |
| Fri10 Apr2020 |
| | 10:00 | Cricket Year 9, Year 8 | v Midlands Tour | A |
| |
| Sat11 Apr2020 |
| | 14:00 | Cricket Year 9, Year 8 | v Midlands Tour | A |
| |
| Sun12 Apr2020 |
| | 10:00 | Cricket Year 9, Year 8 | v Midlands Tour | A |
| |
| Mon13 Apr2020 |
| | 10:00 | Cricket Year 9, Year 8 | v Midlands Tour | A |
| |
| Tue14 Apr2020 |
| | 10:00 | Cricket Year 9, Year 8 | v Midlands Tour | A |
| |
| Thu16 Apr2020 |
| | 09:00 | Cricket Seniors (Year 11,12,13) | v Pre-Season Training | H |
| |
| Fri17 Apr2020 |
| | 09:30 | Cricket Year 8, Year 7 | v Pre-Season Training | H |
| | 13:00 | Cricket Year 10, Year 9 | v Pre-Season Training | H |
| |
| Sat18 Apr2020 |
| | 10:00 | Cricket 1st XI | v Hampton School | A |
| | 10:00 | Cricket U13A, U12A | v Dulwich Cricket Club | H |
| | 13:30 | Cricket U15A, U14A | v Dulwich Cricket Club | H |
| |
| Wed22 Apr2020 |
|  | | Athletics | Year 11 House Athletics | |
| | 11:30 | Cricket 1st XI | v Incogniti | H |
| |
| Thu23 Apr2020 |
|  | 14:00 | Cross Country Year 6, Year 5, Year 4, Year 3 | v Dulwich Hamlet Junior School | A |
| |
| Fri24 Apr2020 |
|  | 16:00 | Badminton U18 | v OAs | H |
| | 17:30 | Cricket Dusters | v Internal | H |
| |
| Sat25 Apr2020 |
|  | | Rowing | Junior Inter Regional Regatta | Peterborough City RC |
|  | 10:00 | Tennis | v ISL Round 1 & 2 | A |
| | 11:00 | Cricket 1st XI | v Tonbridge School | H |
| | 11:30 | Cricket 2nd XI | v Tonbridge School | A |
| | 12:00 | Athletics | Charterhouse | Charterhouse |
| | 14:00 | Cricket 3rd XI, U14A, U14B, U14C, U14D, U14E | v Tonbridge School | A |
| | 14:00 | Cricket 4th XI, U15A, U15B, U15C, U15D | v Tonbridge School | H |
| |
| Sun26 Apr2020 |
| | 10:00 | Cricket 1st XI | v T20 Tournament | H |
| |
| Mon27 Apr2020 |
| | 13:40 | Tennis Year 9 | v House Competition | H |
| |
| Tue28 Apr2020 |
| | 13:40 | Tennis Year 11 | v House Competition | H |
| |
| Wed29 Apr2020 |
| | | Athletics | Lee Valley Outdoor Schools Cup | |
| | | Athletics | Upper School House Athletics | |
|  | 14:30 | Golf College Team | v Langley Park School for Boys | A |
| |
| Thu30 Apr2020 |
| | 13:40 | Tennis Year 10 | v House Competition | H |
| | tbc | Cricket U15A | v The Netherlands | H |
| |
| Fri1 May2020 |
| | 14:30 | Cricket U11A, U11B, U11C, U11D | v Eltham College | H |
| | 14:30 | Tennis U12 | v Eltham College | A |
| | 14:30 | Tennis U11 | v Eltham College | H |
| | 16:00 | Cricket 1st XI | v Whitgift School | A |
| | 18:00 | Cricket Dusters | v The XI | H |
| |
| Sat2 May2020 |
| | | Rowing | Chiswick Regatta | Dulwich College BC |
| | 09:30 | Cricket U13A, U13A, U13B, U13B, U12A, U12A, U12B, U12B | v St Paul's School | H |
| | 09:30 | Cricket U12C | v DC U12D | H |
| | 09:30 | Cricket U13C | v DC U13D | H |
| | 11:00 | Cricket 1st XI | v St Paul's School | A |
| | 12:00 | Athletics | Guy Butler Shield @ Harrow | Harrow School |
| | 14:00 | Cricket 3rd XI, U15A, U15B, U15C | v St Paul's School | A |
| | 14:00 | Cricket 2nd XI, 4th XI, U14A, U14B, U14C | v St Paul's School | H |
| | 14:00 | Tennis U18, U16, U16B | v Epsom College | A |
| | 14:00 | Tennis U15, U15B, U14, U14B | v Epsom College | H |
| | 14:00 | Tennis U18B | v Epsom College | tbc |
| |
| Mon4 May2020 |
| | 14:30 | Cricket U14A, U14B | v King's College School (KCS), Wimbledon | A |
| | 14:30 | Cricket U14C, U14D | v King's College School (KCS), Wimbledon | H |
| |
| Tue5 May2020 |
| | 14:30 | Cricket U13C, U13D | v Emanuel School | A |
| | 14:30 | Cricket U13A, U13B | v Emanuel School | H |
| | 14:30 | Cricket U10A, U10B, U10C, U10D, U10E, U10F | v St Paul's School | H |
| | 14:30 | Tennis U11, U10 | v St Paul's School | H |
