Simon James Heslop (born 1 May 1987) is an English professional footballer who plays as a midfielder for National League North club Scarborough Athletic. Heslop started his career at Barnsley, signing his first professional deal with the club in 2005. He made just one first-team appearance during his six-year association with the club. During his time at Barnsley, Heslop was loaned out to Conference National club Kidderminster Harriers during the 2005–06 season, and spent the following season on loan with Tamworth. He then spent time on loan with Northwich Victoria and Halifax Town during 2007–08, before having further loan spells at Grimsby Town, Kettering Town and Luton Town respectively. He was released by Barnsley in May 2010, and signed for League Two club Oxford United shortly after.