Jim Haydock's pulled muscle gave an opportunity for reserve team goalkeeper Bernard Head - no relation to Ron - to prove his worth between the sticks and Jock Woods was preferred to Len Cannon, otherwise it was an unchanged side that took on Leatherhead in the first round of the Surrey Senior Cup. Leatherhead had been only been formed after the Second World War, a merger of two local clubs, Leatherhead Rose and Leatherhead United. They were on their way to the second of four consecutive Surrey Senior League titles.

Leatherhead pressed from the start and their kick and rush tactics put the home side off their normal game and it wasn't until the 35th minute that they created a chance worthy of the name. Doug Munday put Ron Head clear and his pass found Freddie Gauntlett. In full flight he kept the ball under remarkable control, beat two defenders and then the goalkeeper, Bristow, with a low drive. Roused, the visitors forced three corners in quick succession and a snap-shot from Tudor almost caught Bernard Head napping, but he bent low to gather and as Stenning rushed in to charge he ducked low and the forward was all that ended up in the net. Collins then sent in a shot that Head could only parry upwards and the ball fell down kindly for Lester, but his header went wide of the post. Re-asserting themselves, Wimbledon forced Bristow to concede two corners from shots by Gauntlett and Ron Head, but there was no further scoring in the first half.

The second-half continued in a similar vein, and Lister kicked cleared off the line after Head was caught out of position. Jack Wallis then forced his way clean through, but his shot was high. Harry Stannard managed to elude his man and unexpectedly hooked in shot that Bristow turned over the crossbar. Leatherhead's boundless enthusiasm and keenness finally got their reward when Collins equalised with a flying shot that went into the net like a bullet, and at this point a shock was on the cards. The home side were stung and in the last ten minutes they pressed for a winner, but were unable to find the decider.

Extra time was called and Wimbledon carried on where they'd left off, and it wasn't long before they re-gained the advantage. Stannard received the ball from Wallis and make for the gap between the full-backs, as Bristow came out to challenge the forward flicked the ball to Gauntlett who was left with an empty goal to roll the ball in to. The final goal came early in the second period of extra time. As had happened many times previously the forward line had been caught offside. Leverington passed the free-kick back to Bristow, who picked the ball up. As the keeper attempted to kick clear Stannard stuck out a leg and the ball hit his boot and rebounded straight into the goal. Despite the visitor's protests the goal stood. The Dons comfortably saw out the remaining minutes, although the last few were played without the assistance of Billy Laws who was carried off after sustaining an injury.