| Sacha Brozel | L | 2019-07-02 | Chepstow School v City of London S | Under 19 Final |
| Aditya Munshi | L | 2019-07-02 | Nottingham HS 1 v Chepstow School | Under 19 Final |
| Nugith Jayawarna | D | 2019-07-03 | Chepstow School v Altrincham Grammar School | Under 19 Final |
| Tharshan Kuhendiran | L | 2019-07-03 | Chepstow School v Wilsons School | Under 19 Final |
| Hannah Kassam | W | 2019-09-15 | Chepstow School v North London Collegiate School 2 | Eton Rapidplay 2019 |
| Christopher Tombolis | L | 2019-09-15 | St Pauls School SW13 v Chepstow School | Eton Rapidplay 2019 |
| James Lindquist | L | 2019-09-15 | Westminster Under School A v Chepstow School | Eton Rapidplay 2019 |
| Alisha Sri-Ram | W | 2019-09-15 | Chepstow School v Hen. Barnett School | Eton Rapidplay 2019 |
| Venetia Sivarajasingam | L | 2019-09-15 | Chepstow School v St johns School A | Eton Rapidplay 2019 |
| Alex Wilson | D | 2020-01-22 | Chepstow School v Queen Elizabeth H B | Under 19 Region 5 |
| Tom Skerrett | W | 2020-02-28 | Hereford Cathedral School v Chepstow School | Under 19 Region 5 |
