Cheltenham vs Chesterfield Preview & Prediction

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Cheltenham Town are expected to be down towards the bottom of League Two once again this season as they face a Chesterfield side aiming for promotion this year.

Kick-off date/time:

How to watch on TV: UK – Sky Sports+ / US – Not televised

How to watch online: UK – Sky Sports+ app / US – Cannot be streamed

Cheltenham vs Chesterfield prediction

Under the management of former Newport County boss Michael Flynn, Cheltenham Town do appear to have one of the weaker and smaller squads in League Two this season. They began their campaign with a slender 1-0 defeat to just-relegated Cambridge United at the Abbey Stadium last weekend.

They now face a Chesterfield side that won the National League title in 2024, before reaching the playoffs in League Two in 2025. That playoff campaign ended in defeat to Walsall but Paul Cook’s Spireites have refined their squad over the summer and they began their season with a 1-0 defeat of Barrow in Derbyshire last week.

Cheltenham will believe they can make things tough at Whaddon Road this weekend, but Chesterfield have to be viewed as the firm favourites for this one.

Cheltenham vs Chesterfield tip: Chesterfield to win