Few changes were needed to the team in the 1938-1939 season other than to replace Stan Eastham who had left the club in May, having signed professional forms with Liverpool. As usual Lionel Thornton had other footballing commitments, including with Millwall, but was generally present for Kingstonian in the current campaign, and Bill Whittaker had returned from the F.A. World Tour to resume his place at Centre Half. More controversial was the decision to keep Grahame Lindsay in goal after Cyril Longman returned from the same year long tour. As a result Longman joined St. Albans and there were unfavourable comparisons made when K's played St. Albans in January with many of the opinion that local hero Longman should have regained his old jersey.

One significant addition came in the forward line with Lloyd Stone arriving from Woking. He scored 5 goals on his debut and ended up top scorer with 29 goals in 24 games.

There was a remarkable start to the season, with K's winning their first 5 league games and scoring 26 goals in their first 7 games, including a 5-1 win in the London Charity Cup against rivals Wimbledon. The first setback came in the F.A. Cup where they were beaten in a home replay by Metropolitan Police, having been winning the away game 2-0 with 13 minutes remaining. League form remained good and in the thirteen league games played in the first half of the season, K's were to lose only one and draw one other.

Their long period of failure in the London Senior Cup continued with defeat in the first round by Barnet. Having saved the first game at home after a 3-1 deficit was pulled back to 3-3, they were beaten 3-0 in the replay. However they made good progress in both the Surrey Senior Cup and Amateur Cup. K's reached the 4th Round of the Amateur Cup but a tricky visit to Willington saw them defending bravely and holding out until the 80th minute when a wicked deflection was enough to beat Lindsay. Lindsay, who often showed erratic form, had played "the game of his life" and it was a cruel blow for him to be beaten in such a manner. Stone, who despite his scoring record was another player considered to be inconsistent, also missed several easy chances.

The trip to the North East, which was always a struggle in those days, had K's and Ilford players sharing a train as both had a game in the area and fans joined them on the discounted journey. K's had made an offer for the game to be switched to Richmond Road and a share of a "guaranteed" £250 but Willington rejected the offer and in the end a crowd of 4,794 was perhaps not too far from what could have been expected at Richmond Road, despite unlikely assertions that Kingstonian had had a crowd of 10,000 a few weeks previously against Ilford.

In the Surrey Senior Cup K's progressed to the final with a fine semi-final win at Dulwich and ended the season lifting the trophy by beating Wimbledon 3-2 at Crystal Palace. K's had taken a 3-0 lead within 18 minutes of the start, but Wimbledon recovered and 15 minutes after the interval had got their two goals. K's were able to hold out and lifted their first cup trophy since the 1934-1935 season.

While they didn't have a huge fixture congestion to deal with at the end of the season, the distraction of cup competitions did appear to affect their league form and a title they seemed almost certain to win at Christmas slipped away from them. The title was still very much in their grasp until a run of 4 games without a win in mid to late April put paid to any hopes they had. Eventually they were to finish in 3rd place and 3 points behind Leytonstone who were crowned champions for the second season running.

Wartime
1937-1938

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