Saturday, 02 September 1950
F.A. Cup - XP
Chertsey Town
1 (0) - (1) 3

Apoor run of results in previous seasons meant Wimbledon entered the F.A. Cup at the Extra Preliminary stage for the first time since the 1922/23 season, and the draw saw them paired with Surrey Senior League side Chertsey, their first visit since the West Surrey League days of 1908/09, although the home side had since moved to their Alwyn’s Lane ground in 1929. Pat Field and Arthur Maggs had both returned from holiday and were selected at full back in place of Bill Cousins and J Baldock.

The home side promised to go all out from the first whistle, and they didn’t disappoint. Twice in the first five minutes they could have scored twice. The former Woking player Ballerino, now captain of Chertsey, tricked Ken Lister to get clean away, but delayed his shot and Maggs was able to block him, then a shot from Gray beat Jim Haydock and needed a Wimbledon defender on the line to clear from under the crossbar. The Dons soon worked out a system to combat the kick and rush tactics employed by the hosts and were rewarded in the tenth minute when Freddie Gauntlett headed home a cross from Harry Bull to give them the lead. Town’s do or die tackling prevented the visiting forwards from getting into their proper stride and they resorted to pot-shots. The best came from Jack Wallis and, wind assisted, came in at tremendous speed, but Shepherd " a forward who had only converted to goalkeeper two years before " turned it over for a corner. Bull should have increased the lead before the break, but put it over the bar when he had ample time to walk it in.

Five minutes after the break the second goal came. Smart passing between all five forwards ended with Bull tapping the ball to Harry Stannard, whose flick on left Gauntlett with only the keeper to beat. Grim determination by Chertsey’s defenders kept the game alive, but the Dons could have added to their tally, particularly when right-back Turner flew back at top speed to deflect Gauntlett’s shot for a corner. Wimbledon furthered their advantage in the seventieth minute when Doug Munday lobbed in a high centre from distance. Stannard bet the keeper to the ball and it went over the custodian and into the net. Smith then shot narrowly wide and Gauntlett could only find the keeper’s hands when trying to shoot wide of him. Chertsey never gave up and Ballerino paved the way for their consolation goal, eluding the challenge of Lister and splitting both full-backs with a pass to Barkham. His prompt cross found Cooper on the opposite wing and his shot beat Haydock.