Sheffield born centre half Sid Helliwell began his football career with Wycliffe, from where he was signed by hometown Second Division club Sheffield Wednesday as a centre forward in 1923, Helliwell spending three seasons on the books at Hillsborough without making a first team appearance. After his release by Wednesday he joined Second Division club Reading, making his Football League debut against Manchester City in September 1926, scoring the only goal in a 1-0 victory. He scored once more for Reading in 4 further matches that season and it was at Reading that he converted to centre half, before a move to First Division club Tottenham Hotspur in 1927.
Very much a fringe player at White Hart Lane, he made the only 2 top flight appearances of his career during Tottenham’s 1927-28 relegation season, and played in 7 matches during their first Second Division campaign in 1928-29, but in July 1929 close season he was again on the move, joining Third Division (South) club Walsall, signed along with Spurs teammate Tommy Muldoon.
It was at Hillary Street that Helliwell enjoyed the most productive period of his career, spending three seasons as a regular in their first eleven, scoring 9 goals in 105 appearances for The Saddlers, but in May 1932 he dropped into non league football when he joined Hednesford Town. He returned to Football League action with a brief spell at Halifax Town, making a single appearance for The Shaymen in May 1934, before joining Yorkshire League club Goole Town later that year, his last known club before his eventual retirement.