| | 01/05/2009 | Bickley Park CC - Under 12 Vs Old Wilsonians CC - Under 12 | League | 1 | 9* | 2 | 0 | 9 | 0 | 0 | 0 | 0 | 0 |
| | 08/05/2009 | Bexley CC - Under 11 A Vs Old Wilsonians CC - Under 11 | League | 1 | 4 | 3 | 0 | 7 | 0 | 0 | 0 | 0 | 0 |
| | 20/05/2009 | HSBC, Kent - Under 11 Vs Old Wilsonians CC - Under 11 | League | 1 | 25* | 4 | 0 | 12 | 2 | 0 | 0 | 0 | 0 |
| | 27/05/2009 | OD CUACO - Under 12 Vs Old Wilsonians CC - Under 12 | League | 1 | 9* | 3 | 0 | 9 | 0 | 0 | 0 | 0 | 0 |
| | 04/06/2009 | Old Wilsonians CC - Under 11 Vs Old Colfeians CC - GJCA Under 11A | League | 1 | 4 | 2 | 0 | 2 | 0 | 0 | 0 | 0 | 0 |
| | 12/06/2009 | Bromley Common CC - Under 13 Cup Vs Old Wilsonians CC - Under 12 | League | 1 | 6 | 3 | 0 | 14 | 1 | 1 | 0 | 0 | 0 |
| | 13/06/2009 | Sidcup CC - U11A Vs Old Wilsonians CC - Under 11 | League | 1 | 0 | 4 | 0 | 17 | 1 | 0 | 0 | 0 | 0 |
| | 18/06/2009 | Old Wilsonians CC - Under 11 Vs Dartford CC - Under 11 A | League | 1 | 1 | 3 | 1 | 5 | 2 | 0 | 0 | 0 | 0 |
| | 01/07/2009 | Old Wilsonians CC - Under 11 Vs Bromley CC - Under 11 | League | 1 | 9 | 4 | 0 | 22 | 0 | 0 | 1 | 0 | 0 |
| | 09/07/2009 | Old Wilsonians CC - Under 11 Vs Blackheath CC, Kent - Under 11A | League | 1 | 11 | 2 | 0 | 10 | 1 | 0 | 0 | 0 | 0 |
| | 14/07/2009 | Beckenham CC - Under 11 Broncos Vs Old Wilsonians CC - Under 11 | League | 1 | 2 | 3 | 2 | 2 | 1 | 0 | 0 | 0 | 0 |
| | 18/07/2009 | Orpington CC - 4th XI Vs Old Wilsonians CC - 5th XI | League | 1 | 16 | 2.3 | 1 | 3 | 3 | 0 | 0 | 0 | 0 |
