Swindon Town have completed the signing of Chesterfield midfielder Darren Oldaker on a free transfer.
The 26-year-old has signed a two-year deal at the County Ground, with an option for a third, after leaving the Spireites following their National League play-off campaign.
Promotion Winner Makes League Two Switch
Oldaker joins the Robins after three seasons with Chesterfield, where he made over 100 appearances and played a key role in their 2023/24 National League title-winning campaign. Although he did not feature regularly in the latter stages of the most recent season, he leaves the club with significant experience and pedigree at non-league and EFL level.
The midfielder was one of several players released by Chesterfield in their retained list, which was published on Friday morning. The Derbyshire club are preparing for another promotion push following their play-off disappointment, and Oldaker’s departure marks the end of a successful spell in North East Derbyshire.
Speaking after the move was announced, Oldaker said:
“I’m thrilled to be here and eager to get started. Swindon is a club with great ambition and a family club with great values and supporters. As soon as I heard of the interest, it was a move I couldn’t turn down.”
Oldaker also revealed that conversations with head coach Ian Holloway were crucial in persuading him to make the switch to Wiltshire.
“Every conversation I’ve had with Ian Holloway has really resonated with the style of football I want to play, and the ambition of the manager and the club perfectly aligned with me. I can’t wait to meet the supporters and play at our incredible stadium.”
The midfielder had previously played for Gillingham and Billericay Town before joining Chesterfield in 2022, where he quickly became a key part of Paul Cook’s squad. Known for his composed presence on the ball and tactical intelligence, he is expected to bring calm and leadership to Swindon’s midfield.
Swindon endured a turbulent 2024/25 campaign, struggling in the early months before Ian Holloway took charge and guided them to a mid-table finish. With expectations growing for a top-seven challenge next term, the club is keen to add experienced Football League professionals, and Oldaker’s signing ticks that box.
Writer’s View
This is a sensible move for both club and player. Darren Oldaker offers Swindon Town a ready-made League Two midfielder with leadership experience and a winning mentality.
For Oldaker, the opportunity to reunite with a high-profile manager like Ian Holloway in a more prominent role will appeal, especially after a quieter finish to his Chesterfield career. With the Robins looking to push up the table next season, this signing could prove one of their shrewdest bits of business this summer.
