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The club was established in 1917 by a merger of Chesham Town and Chesham Generals. The new club joined the Spartan League in 1919, which the Generals had been members of prior to World War I. They won back-to-back league titles in 1921–22 and 1922–23, and were champions again in 1924–25. League reorganisation in 1928 saw them placed in Division One West. However, the following season saw them placed in the Premier Division after further reorganisation, and they were league runners-up in 1929–30, before going on to win the league in 1932–33. During World War II they played in the Great Western Combination.

When the league resumed after the war, Chesham were placed in the Western Division of the Spartan League for the 1945–46 season. The league was reduced to a single division for the 1946–47 season, after which the club switched to the Corinthian League. They were runners-up in 1960–61 and 1961–62, but the league disbanded in 1963 and together with the majority of clubs in the league, Chesham were founder member of the new Division One of the Athenian League. In 1966–67 the club reached the first round of the FA Cup for the first time, losing 6–0 at Enfield. The following season saw them reach the final of the FA Amateur Cup, losing 1–0 to Leytonstone at Wembley Stadium. Another FA Cup first round appearance in 1968–69 ended with a 5–0 defeat at Colchester United.

In 1973 Chesham switched to Division Two of the Isthmian League, which was renamed Division One in 1977. They reached the FA Cup first round again in 1976–77, losing 2–0 at Brentford. In 1979–80 the club progressed beyond the FA Cup first round for the first time; after beating Minehead 2–1 in the first round, they defeated Merthyr Tydfil 3–1 in a second round replay, before losing 2–0 at home to Cambridge United in the third round. A fifth appearance in the first round in 1982–83 resulted in a 1–0 defeat by Yeovil Town. The club were relegated to Division Two North at the end of the 1985–86 season, but won the division at the first attempt and were promoted back to Division One.

The 1990–91 season saw Chesham win Division One, earning promotion to the Premier Division. They went on to win the Premier Division in 1992–93, but were denied promotion to the Football Conference due to their ground failing to meet the necessary criteria. The club were subsequently relegated back to Division One at the end of the 1994–95 season, although they did reach the FA Cup first round, losing 1–0 to Bashley. However, they returned to the Premier Division after winning Division One in 1996–97. Following relegation to Division One North at the end of the 2002–03 season, the club finished fourth in 2003–04, earning promotion back to the same level, although they were transferred to the Premier Division of the Southern League.

Chesham finished bottom of the Southern League Premier Division in 2005–06, resulting in relegation to Division One South & West. After one season in the division they were transferred to Division One Midlands. A fifth-place finish in 2008–09 saw them qualify for the promotion play-offs, in which they lost 2–1 to Nuneaton Town in the semi-finals. They reached the play-offs again the following season with a fourth-place finish, and after beating Burnham 1–0 in the semi-finals, they defeated Slough Town 4–0 in the final to earn promotion back to the Premier Division.

The club went on to qualify for the Premier Division promotion play-offs in 2011–12, losing 3–2 to AFC Totton in the semi-finals. The following season resulted in another play-off qualification, this time losing 2–0 to Hemel Hempstead Town in the semi-finals. A third successive play-off campaign was secured when they finished as Premier Division runners-up in 2013–14, but after beating Stourbridge 2–1 in the semi-finals, they lost 3–1 to St Albans City in the final. The following season saw them reach the first round of the FA Cup for the first time since 1994, and after beating Bristol Rovers 1–0, they were beaten 4–0 by Bradford City in the second round. In 2016–17 another first round appearance resulted in a 2–1 defeat at Peterborough United.

At the end of the 2017–18 season Chesham were placed in the Premier Division South due to league reorganisation. They finished fifth in 2022–23 and qualified for the promotion playoffs, but lost 1–0 to Bracknell Town in the semi-finals. The following season they were Premier Division South champions.