Jack Ashton joined the Diamonds on a dual registration basis with Stamford AFC in March 2014. He joined the Daniels in 2013 from Banbury United, with whom he had two spells either side of playing for Oxford City. He originally joined Banbury from Cogenhoe United, having previously had a spell at Long Buckby. He appeared in the final six games of the season in 2013/14, and won the April 2014 Player of the Month award. He picked up two further Player of the Month Awards in 2014/15, and also won the Fans’ Player of the Season award as well as the Players’ Player of the Season trophy. Despite injury problems during 2015/16 he won two further Player of the Month awards as well as picking up the Goal of the Season award for his late winner that clinched the Hillier Senior Cup. After a promising start to the 2016/17 campaign a further knee injury ended his season in November after just 13 appearances that campaign. After a long lay-off, missing almost all of 2017, he returned to the Diamonds starting line-up at the start of 2018, reaching his century of Diamonds appearances during February 2018.