| Thu25 Apr2019 |
|  | 13:40 | Water Polo Year 11, Year 10, Year 9 | v House Competition | H |
|  | 14:00 | Cross Country Year 6, Year 5, Year 4, Year 3 | v Dulwich Hamlet Cross Country | A |
| |
| Fri26 Apr2019 |
| | 13:40 | Water Polo Year 11, Year 10, Year 9 | v House Competition | H |
|  | 18:00 | Cricket Dusters | v Internal | H |
| |
| Sat27 Apr2019 |
|  | 00:00 | Athletics | Charterhouse | Charterhouse |
| | 09:00 | Cricket U13A, U13B, U13C, U13D, U13E, U12A, U12B, U12C, U12D, U12E | v King's College School (KCS), Wimbledon | H |
| | 11:30 | Cricket 2nd XI | v Tonbridge School | A |
| | 11:30 | Cricket 1st XI | v Tonbridge School | H |
| | 14:00 | Cricket 3rd XI, U14A, U14B, U14C, U14D | v Tonbridge School | A |
| | 14:00 | Cricket 4th XI, U15A, U15B, U15C, U15D | v Tonbridge School | H |
|  | 14:00 | Tennis U18 | v Reed's School | A |
|  | tbc | Rowing | Hammersmith Regatta - Y9-10 | Dulwich College BC |
| |
| Sun28 Apr2019 |
| | 10:00 | Cricket 1st XI | v Nat T20 Tournament | H |
| | tbc | Rowing | Junior Sculling Regatta J16s / Seniors | Dorney Boat Club |
| |
| Mon29 Apr2019 |
|  | 13:00 | Skiing Ski Racing Team | v ISA National Indoor Open Ski Championship | A |
| | 13:40 | Tennis Year 9 | v House Competition | H |
| | 16:30 | Water Polo | v Whitgift & Eltham | A |
| |
| Tue30 Apr2019 |
| | 13:40 | Tennis Year 11 | v House Competition | H |
| |
| Wed1 May2019 |
| | | Athletics | House Athletics Upper School & Year 11 | Home |
| | 12:00 | Cricket 1st XI | v Dulwich Cricket Club | H |
|  | 16:30 | Swimming JS Swimming Galas | v ESSA | A |
| | 16:30 | Water Polo U14 | v SWPL @ Alleyn's School | A |
| |
| Thu2 May2019 |
| | 13:40 | Tennis Year 10 | v House Competition | H |
| | 16:30 | Water Polo U13 | v ESSA Semi Finals | H |
| | 18:00 | Cricket Dusters | v Alleyn's School | H |
| |
| Fri3 May2019 |
| | 14:30 | Cricket U14A | v Ernest Bevin College | A |
| |
| Sat4 May2019 |
| | | Athletics | Tonbridge | Tonbridge |
| | 09:30 | Cricket U13A, U13B, U13C, U12A, U12B, U12C | v St Paul's School | H |
| | 11:00 | Cricket 1st XI | v St Paul's School | H |
| | 14:00 | Cricket 2nd XI, 4th XI, U14A, U14B, U14C | v St Paul's School | A |
| | 14:00 | Cricket 3rd XI, U15A, U15B, U15C | v St Paul's School | H |
| | 14:00 | Tennis U15C, U14C | v Bradfield College | A |
| | 14:00 | Tennis U18, U18B, U16, U16B | v Epsom College | A |
| | 14:00 | Tennis U15, U15B, U14, U14B | v Epsom College | H |
| |
| Sun5 May2019 |
| | tbc | Rowing | Wallingford Regatta J15 / J16 / Seniors | Dorney Boat Club |
| |
| Tue7 May2019 |
| | 14:30 | Cricket U13A, U13B | v Emanuel School | A |
| | 14:30 | Cricket U13C, U13D | v Emanuel School | H |
| | 14:30 | Cricket U10A, U10B, U10C, U10D, U10E | v St Paul's School | H |
| | 14:45 | Tennis U10 | v St Paul's School | H |
| | 16:30 | Tennis U18, U15, U14 | v King's College School (KCS), Wimbledon | A |
| |
| Wed8 May2019 |
| | | Athletics | Southwark Track and Field Championships | Croydon Arena |
| | 13:30 | Cricket Upper School, Year 11 | v House Competition | H |
| |
| Thu9 May2019 |
| | 14:30 | Cricket U15A, U15B | v Emanuel School | H |
| | 16:30 | Swimming Swimming Galas | v London Independent Swimming League: Finals | A |
| |
| Fri10 May2019 |
| | 14:30 | Cricket U12A, U12B | v Emanuel School | A |
| | 14:30 | Cricket U12C, U12D | v Emanuel School | H |
| | 14:30 | Cricket U11A, U11B, U11C, U11D | v St Paul's School | A |
| | 18:00 | Cricket Dusters | v Old Alleynians | H |
| |
| Sat11 May2019 |
| | | Athletics | Guy Butler Shield @ Harrow School | Harrow School |
| | 09:30 | Cricket U13D, U12D | v Epsom College | A |
| | 09:30 | Cricket U13A, U13B, U13C | v Hampton School | A |
| | 09:30 | Cricket U12A, U12B, U12C | v Hampton School | H |
| | 11:00 | Cricket 1st XI | v Hampton School | H |
| | 14:00 | Cricket 2nd XI, U14A, U14B, U14C | v Hampton School | A |
| | 14:00 | Cricket 3rd XI, U15A, U15B, U15C | v Hampton School | H |
| | tbc | Rowing | Bedford Regatta - Y9-13 | Bedford RC |
| | tbc | Rowing | Notts City Regatta J16s / Seniors | Loughborough Students RC |
| |
| Sun12 May2019 |
| | tbc | Rowing | Ball Cup - Y9-13 | Dorney Boat Club |
| |
| Mon13 May2019 |
| | | Athletics | House Athletics Year 9 | Dulwich College |
| |
| Tue14 May2019 |
| | 14:30 | Cricket U10A, U10B, U10C, U10D, U10E | v Dulwich Prep London | H |
| | 16:30 | Water Polo U11 | v Dulwich Prep London | H |
| |
| Wed15 May2019 |
| | 14:00 | Cricket 3rd XI, 3rd XI | v Claremont Fan Court School | H |
| | 16:30 | Swimming JS Swimming Galas | v LSSA Heats | A |
| | 16:30 | Water Polo U14 | v SWPL | A |
| |
| Thu16 May2019 |
| | | Athletics | House Athletics Year 10 | Dulwich College |
| | 14:30 | Tennis U15, U14 | v Eton College | A |
| | 16:30 | Water Polo U12 | v Whitgift School | H |
| | 18:00 | Cricket Dusters | v Coutts Bank | H |
| |
| Fri17 May2019 |
| | 14:30 | Cricket U11A | v Hill House International Junior School | H |
| |
| Sat18 May2019 |
| | 09:00 | Cricket U13A, U13B, U13C, U13D | v Dulwich Prep London | A |
| | 09:00 | Cricket U12A, U12B, U12C, U12D | v Dulwich Prep London | H |
| | 10:00 | Cricket U14A, U14B | v Brighton College | A |
| | 11:00 | Cricket 1st XI | v Brighton College | H |
| | 13:00 | Cricket 2nd XI, 3rd XI, U15A, U15B | v Brighton College | H |
| | 13:30 | Tennis U18, U18B, U16, U15, U14 | v Charterhouse | A |
| | 14:00 | Cricket U15C, U14C | v Brighton College | A |
| |
| Mon20 May2019 |
| | 10:00 | Cricket U15A | v London Schools Finals Day | H |
| | 14:30 | Cricket U8A, U8B, U8C, U8D | v Eltham College | H |
| | 14:30 | Cricket U14A, U14B | v Emanuel School | A |
| |
| Tue21 May2019 |
| | 15:00 | Cricket U10A, U10B, U10C | v Eltham College | A |
| | 16:00 | Tennis U10 | v Eltham College | A |
| |
| Wed22 May2019 |
| | 16:30 | Water Polo U13 | v Whitgift School | A |
| |
| Thu23 May2019 |
| | 10:00 | Cricket U15A | v LSCA 20/20 Competition | H |
| | 10:00 | Athletics | London Schools Combined Events | Lee Valley Athletics Centre |
| | 15:00 | Cricket U9A, U9B, U9C | v Eltham College | A |
| | 16:00 | Tennis U9 | v Eltham College | A |
| | 16:30 | Swimming JS Swimming Galas | v Dulwich Championships | H |
| | 16:30 | Swimming Swimming Galas | v Dulwich Championships U13, U12, U11 | H |
| | 16:30 | Water Polo U14 | v City of London School | A |
| |
| Fri24 May2019 |
| | 14:30 | Cricket U11A, U11B, U11C, U11D, U11E | v Dulwich Prep London | A |
| | 18:00 | Cricket Dusters | v PG Wodehouse | H |
| | tbc | Rowing | National Schools Regatta J14 / J15 | Dorney Boat Club |
| |
| Sat25 May2019 |
| | tbc | Rowing | National Schools Regatta J15 / J16 / Seniors | Dorney Boat Club |
