A further halt in football took place during the Great War but soon after, in 1919, the club joined the Surrey Intermediate League where it stayed, uneventfully, until 1939 and a further break. An invitation to become founder members of the Surrey Senior League was not taken up in 1923 but membership was later assumed, on attaining senior status in 1946.

The club has played at various locations within the parish (Willow Walk, Free Prae Road Staines Lane and Chilsey Green before settling down at the present home in 1929. The suffix Town was added to its title some 21 years later. The ground was donated by Sir Edward Stern as a football ground to the premier club in the parish. Next door, a similar trust provides facilities for Chertsey Cricket Club.

Although Chertsey gained membership of the Surrey Senior League immediately after the Second World War, it was not until the 1959/60 season that success came with the league championship. This was repeated twice in the next three years, a halcyon period when the League Cup was also won on three occasions.

Due to the static nature of amateur football in those days, the club could not progress to the preferred Corinthian League so, in 1963, it controversially decided to turn professional and enter the Metropolitan League. Although an entertaining three years were then enjoyed, the cost was too much to bear and a return to the lower levels of the Greater London League for one season occurred before a further shift to the Spartan League was made in 1967.

Indifferent results then dogged the club for almost two decades. This situation was briefly relieved in 1974/75 when the club were league and league cup runners up to an up an coming Farnborough Town. Meanwhile, the fabric of the club was being built up behind the scenes and despite lack of prominence on the park, movement was made via the London Spartan (1975/76) and Athenian leagues through to the Isthmian family with a place in Division Two South in 1984. Instant relegation to the Combined Counties League was suffered but a rejuvenated side won promotion back to the Isthmian ranks within the year whilst winning the League Cup on the way.

The club was rewarded with good league positions but further promotion was denied at first. The worst season after returning to the Isthmian Leagues came when the two Division Twos were split in 1991 and a place in the new Division Three had to suffice. This position was quickly rectified with a runners up slot in 1996. The club also reached the quarter finals of the FA Vase, emulating a similar performance in 1987/88. In 1997, 102 points and a runners up promotion place to Division One was secured. The League Cup was also captured together with the Carlsberg Trophy in the same campaign along with the League Charity Shield.

Success continued and in 1998 third place was attained in Division One and with it further promotion, to the Premier Division. The first season in the Premier Division was one of consolidation but the second was far more difficult. Despite a late rally, it proved insufficient to avoid the drop to Division One. The next two Division One campaigns were similar in nature to each other and saw the side comfortably occupy positions in the top half of the table, finally finishing just over the half way mark each time. However, more difficulties ensued and, in the 1999/00 season the club were relegated to the Second Division as they finished a full eight points from safety. They entered the newly formed Division One South in 2002/03 but, unfortunately, the club's fortunes remained the same as they finished rock bottom, only accumulating 16 points all season, and conceding a whopping 139 goals in the process.