Molesey then moved up to Division One of the Southern Suburban League. However, the cost of travelling led to the club resigning from the league after a single season, dropping into the Kingston & District League. The remainder of the 1920s was a successful period for the club as they won the league and the Teck Cup four times, the Surrey Junior Charity Cup three times in a row between 1926–27 and 1928–29, the Chambers Cup twice and the League Cup once. In the 1933 the club moved up to the Central Division of the Surrey Intermediate League. In 1939 another merger saw Molesey and Molesey Athletic of the Kingston & District League amalgamate to form Molesely United. The new club played in the Kingston & District League, winning it in 1939–40 and 1940–41.