| Tue2 Jun2020 |
|  | 14:15 | Cricket U15B | v Bethany School | A |
| |
| Wed3 Jun2020 |
| | 10:00 | Cricket U12A | v Ashford School | H |
|  | 13:45 | Tennis U13A | v Benenden | A |
| | 15:15 | Cricket U13B, U13C, U13D, U13E, U13F | v Ashford School | A |
| |
| Thu4 Jun2020 |
|  | 14:30 | Golf 1st | v Eastbourne College | H |
| |
| Sat6 Jun2020 |
| | 13:00 | Cricket 1st XI, U15A, U14B, U13A, U13B | v The Judd School | H |
| | 13:30 | Tennis U18A, U18A, U15A, U15A, U14A | v Cranbrook School | A |
| | 14:00 | Cricket 2nd XI, U15B, U14A | v The Judd School | A |
| | 14:30 | Cricket U14A | v St Lawrence College | A |
| | 14:30 | Cricket U15A | v St Lawrence College | H |
| |
| Wed10 Jun2020 |
| | 13:45 | Tennis U12A | v Benenden | A |
| | 14:00 | Cricket U13B | v Junior Kings Canterbury | H |
| | 14:00 | Cricket U13C | v SVPS Boys-U11A | tbc |
| | 14:00 | Cricket U13D | v SVPS Boys-U11B | tbc |
| | 14:00 | Cricket U13E | v SVPS Boys-U11C | tbc |
| | 14:15 | Cricket U13A | v Junior Kings Canterbury | A |
| |
| Sat13 Jun2020 |
| | 09:30 | Cricket U13A, U13B, U13C, U13D | v Epsom College | A |
| | 09:30 | Cricket U12A, U12B | v Epsom College | H |
| | 10:00 | Cricket U12C, U12D | v Epsom College | H |
| | 10:00 | Cricket U13C | v Epsom College | tbc |
| | 11:30 | Cricket 1st XI | v The King's School, Canterbury | H |
| | 12:30 | Tennis U18A, U18A, U18B, U18C | v City of London Freemen's | H |
| | 13:45 | Tennis U15A, U15B, U14A, U14B, U13A, U13B, U12A, U12B | v City of London Freemen's | A |
| | 14:00 | Cricket U15A, U14A | v Epsom College | H |
| | 14:00 | Cricket 2nd XI, U14A, U14B | v The King's School, Canterbury | A |
| | 14:00 | Cricket U15A, U15B | v The King's School, Canterbury | H |
| |
| Tue16 Jun2020 |
|  | 11:00 | Cricket Sixes U13A | v Surbiton High School | A |
| | 12:30 | Cricket Sixes U13A | v Dunottar School | A |
| |
| Wed17 Jun2020 |
| | 14:30 | Cricket U13B, U13C | v Sevenoaks School | A |
| | 14:30 | Cricket U13A, U12A | v Sevenoaks School | H |
| |
| Thu18 Jun2020 |
| | 14:30 | Cricket U13A | v Aldro | H |
| | 14:30 | Golf 1st | v Tonbridge School | H |
| |
| Sat20 Jun2020 |
| | 10:00 | Tennis U13A, U12A | v Epsom College | H |
| | 12:00 | Cricket 1st XI | v Skinners' School | H |
| | 13:00 | Cricket U15A, U14A, U14B | v Skinners' School | H |
| | 14:00 | Cricket 2nd XI, U15B | v Skinners' School | A |
| | 14:00 | Tennis U15A, U14A | v The King's School, Canterbury | A |
| | 14:00 | Tennis U18A, U18B, U18C | v The King's School, Canterbury | H |
| | tbc | Cricket U15A, U15B, U14A, U14B | v Colfe's School | tbc |
| |
| Sun21 Jun2020 |
| | 11:30 | Cricket 1st XI | v Band of Brothers | H |
| |
| Tue23 Jun2020 |
| | 14:00 | Cricket 1st XI | v Somerset College | H |
| |
| Thu25 Jun2020 |
| | 10:30 | Cricket U14A | v Twenty/20 Tournament | A |
| | 10:30 | Cricket U15A | v Twenty/20 Tournament | H |
| |
| Fri26 Jun2020 |
| | 10:00 | Cricket 1st XI | v The King's School, Canterbury | A |
| | 10:00 | Cricket 1st XI | v 1st XI Twenty/20 Tournament | A |
| |
| Thu2 Jul2020 |
| | 10:00 | Cricket U13A | v U13A 10 over Tournament | A |
| | 11:30 | Cricket 1st XI | v Headmasters XI | H |
