On the half-hour Rosedale's Ryan Hewison fired the visitors ahead against the run of play, this became 2-0 after the break, Hewison netting after a Shaun Spozio free-kick, but not before Rosedale had been reduced to 10 men, with Jon Turnbull dismissed, writes Dan Lewis.
A fine individual goal from Morgan Kendrew gave Heslerton late hope, then in the dying moments Ethan Chan volleyed home the equaliser.
Jack Pinder’s penalty for Heslerton was saved by Adam Durrant first up, and although no more would be missed Durrant would hit Rosedale’s fifth and winning kick.
Man of the Match for Heslerton was Sam Besau.
Goldsborough bagged a 2-1 home win against Kirkdale.
Boro took a 15th-minute lead when a Phil Spencer free-kick was headed back across goal in off the post by Andy Martin. The latter then turned provider as a flick-on from a throw found Damon Craig who lashed home a second.
Ten minutes into the half Kirkdale were reduced to 10 men after a late challenge on Martin, but Jack Campbell-Carter’s goal made it a nervy end although Boro managed to hold on.
Bagby & Balk earned a 3-1 home win against Whitby Fishermen’s Academy, Ben Rushworth scoring twice for the hosts, with Kyle O’Gorman also on target.
Ryedale beat Thornton 2-1, Goal Sports winning by the same scoreline at Sinnington.
The Slingsby v Amotherby & Swinton Reserves Division Two game ended in a 1-1 draw.
Slingsby took the lead in the first half when Anthony Taylor fired home, Amotherby levelled through Andy Tiffney.