| Mon5 Jun2023 |
|  | 14:15 | Cricket U15B | v Radnor House Sevenoaks | A |
| | 14:15 | Cricket U15A | v Radnor House Sevenoaks | H |
|  | 16:30 | Tennis U13A, U13A | v Kent College | H |
| |
| Tue6 Jun2023 |
|  | 14:10 | Golf Mixed U18A | v Eastbourne College | A |
| | 14:30 | Tennis U18A, U18B, U18C | v Eton College | A |
| | 16:15 | Tennis U15A | v Bromley High School | H |
| | 16:30 | Tennis Mixed U15A | v Radnor House Sevenoaks | H |
| |
| Wed7 Jun2023 |
| | 14:30 | Cricket U13A, U12A | v St Lawrence College | H |
| | 14:30 | Cricket U13B | v Saint Ronan's School | A |
| | 14:30 | Cricket U13A, U13C, U13D, U13E | v Saint Ronan's School | H |
| | 14:30 | Cricket U13A, U13C, U13D, U13E | v Saint Ronan's School | H |
| | 15:15 | Tennis U15A, U15B, U13A, U13B | v Norton Knatchbull Grammar School | H |
| | 17:45 | Cricket | v King’s Hill | H |
| |
| Thu8 Jun2023 |
|  | 08:00 | Athletics | English Schools Cup Regional Final - Inter Boys/Girls & Junior Girls | Medway Park, Mill Road, Gillingham ME7 1HF |
| | 14:30 | Cricket U15A | v Maidstone Grammar School | A |
| | 15:00 | Cricket U14A, U14B | v Hurstpierpoint College | A |
| |
| Fri9 Jun2023 |
| | 14:00 | Athletics | Athletics Mixed Y8 v Sutton Valence (H) | Sevenoaks School, Kent, TN13 1HU |
| | 14:30 | Tennis U13A, U13A | v Radnor House Sevenoaks | A |
| | 14:45 | Tennis U12A, U12A | v Kent College | A |
|  | 16:15 | Basketball U14A | v John Fisher School | H |
| |
| Sat10 Jun2023 |
| | 08:00 | Athletics | Athletics Boys & Girls: Kent Schools Track & Field(A) Medway Park | Medway Park, Gillingham ME7 1HF |
|  | 09:00 | Sailing Mixed U18A | v Sailing BSDRA Thames Valley Championships | A |
| | 12:30 | Tennis U18A | v Eastbourne College | A |
| | 13:30 | Tennis U18A, U18A, U18B, U18B | v Brentwood School | A |
| | 13:30 | Tennis U15A, U15A, U15B, U15B, U14A, U14A, U14B, U14B | v Brentwood School | H |
| | 14:00 | Cricket 2nd XI, U15A, U15B | v The Judd School | A |
| | 14:00 | Cricket 1st XI, U14A, U14B | v The Judd School | H |
| |
| Mon12 Jun2023 |
| | 14:30 | Cricket U15A, U15B | v Wilson's School | H |
| | 16:15 | Basketball U17A | v John Fisher School | H |
| |
| Tue13 Jun2023 |
| | 11:00 | Cricket 1st XI | v Free Foresters | H |
| | 14:30 | Golf Mixed U18A | v Charterhouse | A |
| | 17:00 | Basketball U13A, U12A | v Whitgift School | H |
| |
| Wed14 Jun2023 |
| | 14:00 | Cricket U13C, U13D | v Lingfield College | A |
| | 14:00 | Cricket U13A, U13B | v Lingfield College | H |
| | 14:15 | Cricket U13A, U13B | v Sutton Valence School | H |
| | 14:30 | Cricket U13C, U13D | v Sutton Valence School | A |
| | 14:30 | Tennis U13B, U13B | v Junior King's School | A |
|  | 16:30 | Volleyball U18A, U18A | v Rikkyo School in England | H |
| | 17:45 | Cricket Orbillians staff | v Sevenoaks Vine Smashers | A |
| | tbc | Tennis U13A | v Junior King's School | tbc |
| |
| Thu15 Jun2023 |
| | 14:30 | Cricket U14A, U14B | v Wilson's School | H |
| | 15:00 | Cricket U14A, U14B | v Mayfield School | A |
| | 15:30 | Cricket U14A, U14B | v Mayfield School | H |
| |
| Fri16 Jun2023 |
| | 08:30 | Athletics | Kent IAPS Championships - Year 7 & 8 | Julie Rose Stadium - TN24 9QX |
| | 14:30 | Cricket U13A, U13B | v Wilson's School | A |
| |
| Sat17 Jun2023 |
| | 09:00 | Sailing Mixed U18A | v Oakham School | A |
| | 09:00 | Sailing Mixed U18A, U16A | v Sailing Hoad Shield | A |
| | 11:30 | Cricket 1st XI | v The King's School, Canterbury | A |
| | 13:30 | Athletics | Athletics Boys Y9,10,12 A String v Tonbridge School (A) | Tonbridge School, Kent, TN9 1JP |
| | 14:00 | Cricket 1st XI, U14A, U14B | v The King's School, Canterbury | A |
| | 14:00 | Cricket 2nd XI, U15A, U15A, U15B, U14A | v The King's School, Canterbury | H |
| | 14:00 | Tennis U18A | v Quadrangular | A |
| | 14:00 | Tennis U15A, U14A | v Quadrangular | H |
| | 14:30 | Tennis U18A, U18B, U15A, U15B, U14A, U14B | v Eastbourne College | tbc |
| |
| Mon19 Jun2023 |
| | 13:00 | Cricket U13A | v Cricket Hardball 8's Tournament | A |
| | 16:45 | Basketball U14A | v Whitgift School | H |
| |
| Tue20 Jun2023 |
| | 11:00 | Cricket U13A | v The Reigate Sixes Tournament | A |
| | 14:30 | Basketball U18A | v Tonbridge School | A |
| | 14:30 | Golf 1st | v Dulwich College | H |
| | 16:15 | Tennis U15A, U14A, U13A, U12A | v Bromley High School | H |
| | 16:30 | Cricket U15A, U15B | v Mayfield School | H |
| | 16:30 | Tennis Mixed U15A | v Radnor House Sevenoaks | H |
| |
| Wed21 Jun2023 |
| | 09:30 | Basketball U13A | v NBA South East Basketball Finals | A |
| | 11:00 | Cricket U13A | v The Reigate Sixes Tournament | A |
| | 14:30 | Cricket U13B, U13C | v Holmewood House School | A |
| | 14:30 | Cricket U13A | v Holmewood House School | H |
| | 17:45 | Cricket Orbillians staff | v Fawkham Guzzlers | H |
| |
| Thu22 Jun2023 |
| | 13:00 | Cricket U15A | v Cricket Hardball 8's Tournament | A |
| |
| Fri23 Jun2023 |
| | 18:00 | Cricket Orbillians staff | v Old Sennockians | H |
| |
| Sat24 Jun2023 |
| | 08:00 | Athletics | Athletics Combined Event Championships *Selected Students ONLY | Lee Valley Athletics Centre, N9 0AR |
| | 12:10 | Athletics | Epsom College Co-Ed Athletics | Epsom College, KT17 4JQ |
| | 13:00 | Cricket 2nd XI, U15A, U15B | v Skinners' School | H |
| | 13:15 | Cricket 1st XI, U14A, U14B | v Skinners' School | A |
| | 14:00 | Tennis Mixed U18A | v Haileybury | H |
| | 14:00 | Tennis U15B, U15B, U15C, U15C, U14B, U14B, U14C, U14C | v The King's School, Canterbury | A |
| | 14:00 | Tennis U18B, U18B, U18C, U18C | v The King's School, Canterbury | H |
| | 14:30 | Tennis Mixed U15A, U14A | v Mixed Doubles | A |
| | 14:30 | Tennis Mixed U18A | v Mixed Doubles | H |
| |
| Sun25 Jun2023 |
| | 13:30 | Cricket 1st XI | v Old Sennockian XI | H |
| |
| Mon26 Jun2023 |
| | 09:00 | Sailing Mixed U18A, U16A | v Sailing BSDRA Finals | A |
| | 14:00 | Cricket U16A | v Newington College (Australia) | H |
| |
| Tue27 Jun2023 |
| | 11:00 | Cricket 1st XI | v Caterham School | A |
| | 14:30 | Cricket 1st XI | v Haileybury | A |
| |
| Wed28 Jun2023 |
| | 10:00 | Brighton Beach Volleyball Tournament Y10-12(A) | Yellow Wave, Brighton |
| | 10:00 | Volleyball U18A, U18A, U18B, U18B | v Brighton Beach Tournament | A |
| |
| Thu29 Jun2023 |
| | 10:00 | Cricket U15A | v Sutton Valence T20 Tournament | A |
| | 10:00 | Cricket U14A | v Sevenoaks T20 Tournament | H |
| | 11:00 | Cricket 1st XI | v St Lawrence College | A |
| |
| Fri30 Jun2023 |
| | 10:00 | Cricket 1st XI | v King's T20 Tournament | A |
| |
| Sat1 Jul2023 |
| | 11:00 | Cricket 1st XI | v MCC | H |
| |
| Sun2 Jul2023 |
| | 14:30 | Sailing Mixed U16A | v Sailing Itchenor Schools Week | A |
