Their home ground was Cuckfield Park and they played in red & black hooped shirts and cricket trousers.

In 1900 they were founder members of the Mid Sussex League along with Burgess Hill, Haywards Heath and East Grinstead & Hurstpierpoint.

In 1905 the club moved to Ockenden Park and in 1911 made their first appearance in the Montgomery Cup Final.

In 1946 their first league championship was secured and a year later they won the Montgomery Cup at the seventh attempt.

Shortly after Cuckfield Town played Brighton & Hove Albion's first team to celebrate their 125th anniversary.

Three years later Cuckfield won their ninth Montgomery Cup and record goalscorer Ray Leaney reached his 500th goal Mid Sussex football.

In 2010 after three seasons restructuring the club from top to bottom the first team completed their climb back to the Premier Division, picking up a Mowatt Cup win on the way.

In 2017, another big change occurred, with a new committee and a new management team taking charge of the 1st XI.

[1] The 1st XI were on course to win Division 2 North in the 2019–20 season, but unfortunately were unable to officially be crowned champions due to the COVID-19 pandemic.