Career
Born in Rotherham, South Yorkshire, Helliwell attended Old Hall Comprehensive School and started his football career as a junior with Sheffield Wednesday. He had trials at Stoke City before joining the reserve team at Chesterfield in 1982, and during his time as a youth player he worked for steel producer British Steel. He moved into non-League football with Matlock Town in 1983, where he scored 68 goals in just over four seasons before joining Third Division team York City for a fee of £10,000 in October 1987. He made his debut in a 4–2 defeat to Sunderland on 24 October and scored his first goal in a 1–1 draw with Bury on 7 November. He finished his first season, 1987–88, with 32 appearances and scored eight goals, while York were relegated to the Fourth Division. He finished the 1988–89 season as York's top scorer with 11 goals, as well as winning the Clubman of the Year award. His only hat-trick for the club came in a 7–1 victory over Hartlepool United in the Football League Trophy and he finished the 1989–90 season again as York's top scorer with 19 goals, featuring in all of York's 54 games. His final season with York, 1990–91, saw him finish as top scorer for a third successive season with 10 goals.
Helliwell joined Scunthorpe United for a fee of £80,000 in August 1991 and he became the first player to miss a penalty kick in a penalty shootout in the FA Cup, which came against Rotherham United. He featured for Scunthorpe in the 1992 Fourth Division play-off Final, which was lost on penalties to Blackpool. He finished as top scorer for the 1992–93 season and before the start of the following season, he joined Rotherham for a fee of £60,000 in August 1993, after making 80 league appearances and scoring 22 goals for Scunthorpe. He played some games as a centre half at Rotherham, where he made 52 appearances and scored four goals in the league before joining Stockport County in January 1995 as a replacement for Kevin Francis. He scored twice on his debut against Hull City and made 39 appearances and scored 13 goals for Stockport before joining Burnley for a fee of £25,000 in February 1996.
He was loaned out to Mansfield Town for a month in September and made his debut in a 0–0 with Doncaster Rovers, eventually scoring his first and only goal in his final game against Carlisle United. Helliwell was soon loaned out again, joining Chester City in October and making his debut in a 0–0 draw with Scarborough, with his only goal coming in a 2–1 victory over Exeter City. His only appearances of the 1997–98 season came during a loan spell at Doncaster Rovers, where he made nine appearances and scored one goal, which came against former loan club Chester. He joined Ilkeston Town in 1998 and featured for them in FA Cup games against Football League sides Carlisle United and Swindon Town.
After returning to semi-professional football, he worked part-time as an electrician. In March 2001, Helliwell was appointed as one of a three-man management team at Ilkeston alongside Chris Marples and former Burnley team-mate Charlie Bishop. The trio guided the club to safety at the end of the season; Marples was consequently hired as manager on a permanent basis, Helliwell returned to his playing role and Bishop left Ilkeston, although would return to manage the side the following year. Helliwell retired from football following the 2001–02 season, having spent four seasons with Ilkeston.
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