In June 2026, the Shrimpers announced the signing of Darren Oldaker for an undisclosed fee from League Two outfit Swindon Town with the midfielder joining on a two-year contract with a club option for a third.

A graduate of Gillingham’s academy, Oldaker earned promotion to the National League with Dorking Wanderers before making the move to Chesterfield. He made more than 110 appearances for the Spireites, playing a major role in the side that earned 98 points en route to the National League title.

In 2025, Oldaker joined Swindon Town and made 39 League Two appearances for the Wiltshire-based outfit. He also netted a 116th-minute winner in the FA Cup Third Round victory over Rotherham United.