Jon Cullen had a couple of stabs at league football. He started out at Doncaster Rovers under Billy Bremner and he spent three years there before drifting into non-league football. His second chance came when Mick Tait brought him to Hartlepool on transfer deadline day, 1997. He arrived with Pools fighting against relegation and played his part in helping to ensure that fight was successful. A skilful midfielder with an eye for goal, Cullen started the next season in sparkling form and soon attracted a number of scouts from higher divisions to the Vic. Sheffield United pushed their interest and Cullen left for Bramall Lane in January 1998, with Pools receiving a fee in the region of £250,000. Despite his early departure, Cullen finished the season as Hartlepool`s top scorer as the club experienced a frustrating season, drawing a record 23 of their 46 games. Cullen never quite reproduced his form of 1997 and spent a lot of his time at Sheffield United on loan to lower division clubs. He eventually left Bramall Lane having failed to make a first team start and, after spells at Peterborough and Darlington, returned to non-league football.