Tom joined Chester on loan from Boston United in February 2025. From Burton upon Trent, Tom has won promotion from the National League North in each of the last two seasons, first with Kidderminster Harriers and then more recently with Boston. He began his career with Walsall and has also had temporary spells with the likes of Salisbury, Bath City and Alfreton Town. This term, Leak made 17 appearances in the National League this season for the Pilgrims.