Formed in 1988, Wealden joined Division 3 of the Sussex County League ten years later, finishing 4th in their first season before gaining promotion as runners-up to Bosham in 1999/00. Since then the club has established itself in senior football, finishing 7th in 2002/03.

The following season was comparatively disappointing, but 2004/05 saw the Oaks achieve their best finish to date. But more greater consistency, they would have finished higher than 5th, although absence of floodlights would have precluded their promotion.

In addition the Wealden picked up the Division Two Challenge Cup, with an emphatic 3-0 win over Midhurst + Easebourne.

On the back of their 2004/05 form, Wealden were strongly fancied by many to be championship contenders in 2005/06. They reached the semi-finals of the Division Two Challenge Cup but had to relinquish their hold on the trophy as they lost 5-4 on penalties to eventual winners Mile Oak (the score having been 2-2 aet). In the League they could only manage 6th. With floodlights now erected, The Oaks may again be a force to be reckoned with under new boss Andy Gander, former Wick and Lancing Manager.