| Date | Opposition | Time | Venue | Manager/Result |
| Sun Jun 5 | Headley | 13.30 | Headley | Cancelled – Rain |
| Sun Jun 12 | Downside Wanderers Cricketer Cup 1st round |
11.00 | Downside | Won by 10 wkts |
| Sun Jun 19 | Radley Rangers | 11.00 | Jubilee | Cancelled |
| Sun Jun 26 | Uppingham Rovers Cricketer Cup 2nd round |
11.00 | Jubilee | Won by 2 wkts |
| Fri Jul 1 | School | 11.00 | Jubilee | Lost by 107 runs |
| Fri Jul 8 | Old Malvernians | 11.00 | Jubilee | Cancelled |
| Sun Jul 10 | Old Wellingtonians Cricketer Cup QF |
11.00 | Wellington | Lost by 2 wkts |
| Sun Jul 10 | Eton Ramblers | 11.00 | Jubilee | Won by 103 runs |
| Mon Jul 11 | Old Johnians | 11.00 | Jubilee | Won by 6 wkts |
| Tue Jul 12 | Old Georgians | 11.00 | Jubilee | Won by 8 wkts |
| Wed Jul 13 | Lancing Rovers | 11.00 | Lancing | Won by 26 runs |
| Thu Jul 14 | Wimbledon | 11.00 | Jubilee | Won by 5 wkts |
| Fri Jul 15 | Old Millfieldians | 11.00 | Jubilee | Lost by 4 wkts |
| Sun Jul 16 | Frogs | 11.00 | Jubilee | Lost by 7 wkts |
| Sun Jul 24 | Flashmen | 11.00 | Jubilee | Lost by 3 runs |
| Thu Jul 28 | Abinger Hammer | 14.00 | Abinger Hammer | Drawn |
| Sun Jul 31 | Sussex Martlets | 11.00 | Jubilee | Cancelled |
| Fri Aug 5 | Blackheath | 14.00 | Blackheath | Tied |