| Charukgan Muhunthan | L | 2019-07-02 | Chepstow School v City of London S | Under 19 Final |
| Abhishek Thakar | W | 2019-07-02 | Nottingham HS 1 v Chepstow School | Under 19 Final |
| Akash Gupta | D | 2019-07-03 | Chepstow School v Wilsons School | Under 19 Final |
| Jenny Zhan | W | 2019-09-15 | Chepstow School v North London Collegiate School 2 | Eton Rapidplay 2019 |
| William PM Lovell | L | 2019-09-15 | St Pauls School SW13 v Chepstow School | Eton Rapidplay 2019 |
| Kameron Grose | W | 2019-09-15 | Westminster Under School A v Chepstow School | Eton Rapidplay 2019 |
| Zahra Shahabuddin | W | 2019-09-15 | Chepstow School v Hen. Barnett School | Eton Rapidplay 2019 |
| Anish Choudhury | L | 2019-09-15 | Chepstow School v St johns School A | Eton Rapidplay 2019 |
| Gabriel Preece | W | 2020-02-28 | Hereford Cathedral School v Chepstow School | Under 19 Region 5 |
| Vishal Pradeep | W | 2020-03-09 | Bristol GS B v Chepstow A | Bristol TCC |
| Daniel Seymour | W | 2020-03-09 | Bristol GS A v Chepstow A | Bristol TCC |
| Jay Mundray | W | 2020-03-09 | Chepstow A v Bristol GS C | Bristol TCC |
| Peter Skeen | W | 2020-03-09 | Churchill A v Chepstow A | Bristol TCC |
