Born in Rotherham, West Riding of Yorkshire,[4] Helliwell attended Old Hall Comprehensive School and started his football career as a junior with Sheffield Wednesday.
[14] He finished as top scorer for 1992–93 with 17 goals from 51 matches, and before the start of the following season, signed for Second Division club Rotherham United on 1 August 1993 for a £50,000 fee.
[5][16] Having made 16 appearances and scored three goals during 1994–95,[17] Helliwell signed for Second Division club Stockport County on 12 January 1995[6] as a replacement for Kevin Francis.
[20] He was loaned out to Third Division club Mansfield Town on 6 September 1996 for one month, and made his debut the following day in a 0–0 away draw with Doncaster Rovers.
[21] Helliwell was soon loaned out to another Third Division club, joining Chester City on 11 October 1996,[6] making his debut a day later in a 0–0 draw away to Scarborough.
[26] Helliwell took over as caretaker manager at Ilkeston after Keith Alexander resigned in October 2000, and led the team to the first round of the FA Cup before John McGovern was appointed in November.
[27] The trio guided the club to safety at the end of 2000–01; Marples was consequently hired as manager on a permanent basis in May 2001 and Helliwell returned to his playing role.