The society holds a yearly philatelic competition  for members.  See the Programme page for the date of this years competition.

The winners for the 2008-2009 season were as follows:

Sloan Cup (best overall entry)
Paul Wright Jamaica: the Queen Victoria Key Types

Patrick Cup (best postal history entry)
Ray Downing Stamp Positioning: A Brief Introduction

Les Child Tankard (best postal stationery entry)
Ray Downing Royal Mail Certificates of Posting with the Royal Mail Cruciform

Ewart Sanders Cup (best stamps only entry)
John Davies Italy and Colonies in Africa

Beach Cup (best thematic entry) 
No entries

The rules of the competition are as follows...

WIMBLEDON AND DISTRICT PHILATELIC SOCIETY COMPETITION RULES

1.  Each entry in the competition shall compete in the General Class but may also be nominated by its owner for one other class.

2.  Any member may submit more than one entry.

3.  Entries in all classes shall consist of twelve sheets, not exceeding 10” x 12”.

4.  Entries may be on any subject to do with philately.

5.  All material in the entry must be the sole property of, and be mounted and written up by, the competitor.

6.  Marks will be awarded as follows:

    a Writing-up and attractiveness of presentation up to 40%

    b Relative condition up to 30%

    c Philatelic knowledge (or knowledge of the subject for the Thematic Class) up to 25%

    d Judge’s discretion up to 5%

7.  Cups will be awarded as follows:

    The best overall entry shall be awarded the Sloan Cup.

    The best thematic entry shall be awarded the Beach Cup.

    The best postal history or aerophilately entry shall be awarded the Patrick Cup.

    The best traditional stamps only entry shall be awarded the Ewart Sanders Cup.

    The best postal stationery entry shall be awarded the Les Child Tankard.

    The best entry from a member who has not previously won any of the Society’s awards shall earn a certificate of merit.

    Trophies will be awarded in the order given above, so that if an entry wins the Sloan Cup it is not eligible to win the Beach, Patrick, or Ewart Sanders Cups or the Les Child Tankard, and the winner of any of these may not receive a certificate of merit.

8.  All trophies are the property of the Society and are awarded for the period until the next competition.