He managed 19 appearances (scoring twice, including Derby's first game back at the top level) during their return to the top flight, but also found himself out on loan at second-tier club Sheffield United to gain more playing time. Wolverhampton Wanderers After failing to feature in the opening months of the Rams' 1997–98 season, he dropped down a division to join Wolverhampton Wanderers initially on a month's loan in October 1997. After impressing with 2 goals in 8 starts, he signed a permanent deal for £75,000. His first season with the club also saw him almost appear in an FA Cup Final, but they lost to eventual winners Arsenal in the semi-final. His second season at Molineux was less successful as he found himself out of the starting line-up in the opening games. He went on loan to nearby Walsall of the Second Division for four months, but returned to Wolves first team when this loan expired. He scored Wolves' final goal of the season in a 3–2 defeat to Bradford City that meant they missed out on the play-offs. Blackpool After a second successive seventh-place finish in a season that saw Simpson feature only sparingly, he signed for Blackpool on a free transfer in August 2000. Here, he helped the club win promotion from the Third Division via the play-offs in his first season but he left during his second, to join Rochdale in March 2002. Just before leaving the club he helped them win the 2001–02 Football League Trophy, playing as a substitute in the final. Rochdale He made nine appearances in the final games of the 2001–02 season for Dale, scoring 6 times. This goal rush helped push the club into the play-offs, where they lost to Rushden & Diamonds (despite another goal from Simpson). Managerial career Rochdale After manager John Hollins departed from Rochdale in 2002, Simpson stepped in as player-manager. He began the season in equally bright goal-scoring form, but as the pressure of management took its toll and he enjoyed a largely unsuccessful season. Simpson left Rochdale after only season in charge where they reached the FA Cup fifth round, an equal club record, but finished 19th after a late turnaround by Macclesfield saw them drop from 13th in the final 10minutes of the season. Carlisle United Following his departure from Rochdale, Simpson moved back to his home town, where he became the manager