Gillingham vs Chesterfield Prediction & Betting Tips (19 August)

Gillingham travel to the SMH Group Stadium to face Chesterfield in a League Two clash that promises tension and tactical intrigue. Under Gareth Ainsworth’s stewardship, the Gills have shown signs of resilience, going six matches unbeaten despite a string of draws. Their recent 2-2 comeback against Salford City highlighted Romeao Hutton’s growing influence on the flanks, while Bradley Dack’s return to fitness adds a creative spark in midfield. Ainsworth, who replaced John Coleman last month, has instilled a more aggressive pressing style, and his side will be eager to convert their defensive solidity into a long-awaited away win—something they’ve failed to achieve in nine attempts this calendar year.

Chesterfield, meanwhile, are licking their wounds after a humbling 4-0 defeat to Tranmere Rovers, a result that snapped their six-game unbeaten run and dented their playoff ambitions. Paul Cook’s men sit 10th in the table, seven points adrift of the top seven, and know that anything less than a win could see them lose further ground. Injuries to key forwards Will Grigg and Paddy Madden have forced tactical reshuffles, with Kane Drummond and Armando Dobra expected to shoulder attacking duties. The midfield remains anchored by the experienced Tom Naylor and Darren Oldaker, while Jamie Grimes leads a defense that has been solid at home, conceding just once in their last three outings at the SMH Group Stadium.



Historically, Gillingham have had the upper hand in this fixture, winning 31 of the 71 meetings between the sides. Their last encounter in August 2024 ended in a 1-0 win for the Gills, courtesy of a Robbie McKenzie strike. However, Chesterfield’s home form and attacking depth—bolstered by the likes of Dilan Markanday and James Berry—make them formidable opponents. The Spireites have lost just once in their last seven home games, and with the crowd behind them, they’ll be determined to bounce back from their recent setback. Expect a high-tempo match with both sides pressing for control early.

Given the form and tactical setups, a 2-1 win for Chesterfield seems the most plausible outcome. Gillingham’s defensive structure may frustrate the hosts initially, but Chesterfield’s urgency and attacking flair should eventually break through. A goal from Dobra or Pepple could tilt the balance, while Gillingham may find consolation through a set-piece or a moment of brilliance from Dack. With playoff hopes flickering for Chesterfield and Gillingham seeking to climb out of mid-table obscurity, this clash could be a turning point for both sides.

• Summary: Gillingham is going head to head with Chesterfield starting on 19 Aug 2025 at 18:45 UTC . The match is a part of the League Two .
• Gillingham Feedinco Rating: 6.71
• Chesterfield Feedinco Rating: 7.01