At Hull, Jobson flourished: over five seasons he made 221 league appearances, scoring 17 goals — establishing himself as a strong, athletic defender with an eye for goal. His performances earned him a move to Oldham Athletic in August 1990 for a club-record £460,000. Jobson became a key figure in the Latics’ promotion to the First Division in 1991, featuring in 189 league matches, scoring 10 goals, and playing in an FA Cup semi-final in 1994. He also won two England B caps in this period.

By October 1995, aged 32, Jobson earned a high-profile move to Leeds United for £1 million under manager Howard Wilkinson. Though it represented a personal milestone — a return to top-flight football and a local big-club — his time at Elland Road would ultimately prove frustrating.

He made 12 league appearances in his first season (1995/96), scoring once — a memorable goal in a 1–1 draw at home to Wimbledon in December. That campaign also featured his standout moment in a famous 3–1 Christmas Eve victory over bitter rivals Manchester United, a game Jobson later described as the highlight of his Leeds stint. That result remains a cherished memory for many supporters .

In his second season (1996–97), he added 10 more league appearances, but the ongoing injury challenges — particularly a knee issue—began to limit his playing time. Leeds also underwent managerial change—Howard Wilkinson left; George Graham took charge and brought in younger defenders like Robert Molenaar, further reducing Jobson’s opportunities. He did not feature at all in the 1997/98 season, and by March 1998 had been loaned to Southend United, where he played eight times and scored once, before Leeds allowed him to leave on a free transfer to Manchester City.

Crucially, despite his ambition and professionalism, injuries curtailed what could have been a more substantial impact at Leeds. Jobson himself acknowledged the frustration, stating in later interviews that his time at Leeds was ruined mainly by physical setbacks despite a promising start and local significance of the move .

After joining Manchester City in March 1998, Jobson reunited with former manager Joe Royle. There, he helped City reach back-to-back promotions—from Division Two to Division One, then into the Premier League — making around 50 league appearances and scoring four goals over three seasons. Later in his career, he had short loan spells at Watford and Tranmere Rovers, finished with permanent moves to Tranmere and then Rochdale, where he played until retirement in 2003 — making a final league appearance just six days before his 40th birthday. In total, his professional career spanned nearly 600 league appearances and 42 goals.

Off the pitch, rather than fading into anonymity after retirement, Jobson transitioned into important football administration roles. In November 2002, while still playing at Rochdale, he succeeded Nick Cusack as chairman of the Professional Footballers’ Association (PFA), a post he held through to his retirement and beyond. He later served as a senior executive in their player management department, shaping support structures for professional footballers in England.