The 29-year-old inked a two-year deal at Bootham Crescent and in the process returns to the city of his birth after turning down a new contract with new league rivals Wrexham.
The 5`11” midfielder began his career with Yorkshire rivals Barnsley, progressing through the youth system and signing professional terms in 2005.
Months later he experienced National League football for the first time while on loan at Kidderminster Harries, and then with Tamworth a year later, before returning to Oakwell in April 2007 and making his debut for the Tykes against West Bromwich Albion.
Further loan spells away from South Yorkshire followed as Heslop spent time at Northwich Victoria, Halifax Town, Grimsby Town, Kettering Town and latterly Luton Town where he featured in both National League play-off semi-final legs against the Minstermen in 2010.
Upon his return to Oakwell from Kenilworth Road that summer, the midfielder left Barnsley and signed for newly-promoted Oxford United.
Over the course of the next three campaigns Heslop made over a century of appearances at the Kassam Stadium. However, after not being offered a new deal to remain with the U’s, he moved up a division to then League One side Stevenage in 2013.
He spent a campaign with Graham Westley’s outfit before doing likewise with Mansfield Town for the 2014/15 season.
After departing Field Mill at the end of his one-year deal last summer, Heslop joined National League outfit Torquay United on a deal until January 2016, before he switched to league rivals Wrexham on a six-month contract.