Round 1
Play-by date: 26 Jan 2019 |
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 | University College School (UC... 1st XI 10:00, Sat 19 Jan 2019 Main School | 1 |  | | 
 | Whitgift School 1st XI | 2 | | | 
 | Kingston Grammar School Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | | | 
 | Latymer Upper School 1st XI 10:45, Sat 26 Jan 2019 Latymer Playing Fields, Wood Lane | 2 | | | 
 | Mill Hill & Belmont Schools 1st XI | 3 | | |
| King's College School (KCS), ... Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | | | 
 | St Paul's School Boys-U18A 14:15, Wed 30 Jan 2019 Main School | 1 | | | 
 | Hampton School 1st XI | 2 | | | 
 | Ardingly College 1st XI Sat 26 Jan 2019 | | | | | Bye | | | | 
 | The John Lyon School 1st XI Wed 16 Jan 2019 | 0 | | | 
 | Brentwood School Boys-U18A | 6 | | | 
 | Epsom College Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | | | 
 | St George's Weybridge 1st XI 14:30, Wed 16 Jan 2019 Leathersellers' Sports Ground | 3 | | | 
 | Colfe's School Boys-U18A | 2 | | | 
 | St John's School, Leatherhead 1st XI Sat 26 Jan 2019 | | | | | Bye | | | | 
 | City of London School 1st XI 14:30, Wed 23 Jan 2019 The Oval | 4 | | | 
 | Dulwich College 1st XI | 5 | | | 
 | RGS, Guildford 1st XI Sat 26 Jan 2019 | | | | | Bye | | | |
| Highgate School Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | | | 
 | Forest School Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | | | 
 | Royal Russell School Boys-U18A 10:00, Wed 16 Jan 2019 | | | | | Bye | | | |
| Westminster School Boys-U18A Sat 26 Jan 2019 | | | | | Bye | | |
| Round 2
Play-by date: 09 Feb 2019 |
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| Kingston Grammar School Boys-U18A 09:30, Sat 2 Mar 2019 Main School | 5 | | |
| Whitgift School 1st XI | 4 | | | | | | |
| Mill Hill & Belmont Schools 1st XI 14:30, Wed 6 Feb 2019 | 2 | | |
| King's College School (KCS), ... Boys-U18A | 0 | | | | | | |
| Hampton School 1st XI 10:00, Sat 9 Feb 2019 | 2 | | |
| Ardingly College 1st XI | 0 | | | | | | |
| Brentwood School Boys-U18A 14:30, Thu 7 Feb 2019 Senior School | 4 | | |
| Epsom College Boys-U18A | 0 | | | | | | |
| St George's Weybridge 1st XI 14:30, Wed 30 Jan 2019 St George's College Main Entrance KT15 2QS | 4 | | |
| St John's School, Leatherhead 1st XI | 3 | | | | | | |
| Dulwich College 1st XI 14:30, Mon 11 Feb 2019 Main College | 4 | | |
| RGS, Guildford 1st XI | 0 | | | | | | |
| Highgate School Boys-U18A 14:15, Wed 6 Feb 2019 Main School | 0 | | |
| Forest School Boys-U18A | 7 | | | | | | |
| Royal Russell School Boys-U18A 14:15, Wed 23 Jan 2019 Main School | 2 | | |
| Westminster School Boys-U18A | 1 | | | |
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