Pressman is best remembered as the long-time goalkeeper of Sheffield Wednesday, where he spent 19 seasons, playing 478 matches in all competitions including the UEFA Cup.
He was unlucky not to play in the 1991 League Cup final victory against Manchester United, as he had played in every round of the competition that year as well as a significant number of league matches until the quarter final stage where he was replaced by more senior goalkeeper and future Wednesday manager Chris Turner.
[5] In July 2005, Pressman was signed by Mansfield Town,[6] at the time managed by his former Sheffield Wednesday teammate Carlton Palmer, and was first-choice goalkeeper for the majority of the following season.
Pressman announced his retirement from the game in July 2006 after being released by Mansfield Town although there were some rumours that he would return to Wednesday in a coaching role.
At the end of September 2006 Pressman signed a short-term deal with Northern Ireland side Portadown, who had a goalkeeping crisis.
Despite training in Doncaster during the week and flying to Northern Ireland for matches, Pressman signed a contract extension with Portadown in late December 2006 that kept him at the club until the end of the 2006–07 season.
Both men, however, lost their jobs in March 2011 after a string of poor results left the Iron deep in relegation trouble.
He is married to Joanne and has three children, Tom - who is also a goalkeeping coach, and in 2019 was signed by Sheffield United Women[17] - Danny and Sophie.
Pressman was awoken by the noise and chased the thief for 15 miles, by car and on foot, before helping police to corner and arrest the man in a field.