The North Riding Senior Cup Semi Final finished 1-1 after 90 minutes, with Whitby winning the penalty shoot-out 4-2 at the King George V Stadium.
Junior Mondal came close to putting Whitby ahead in the first half but his effort hit the cross bar.
The Blues did take the lead on 62 minutes through Captain Dan Rowe.
Guisborough, who play their football lower down the football pyramid in the Northern League, equalised with 12 minutes remaining through Matty Tymon.
With scores level after 90 minutes, it was straight to a penalty shoot-out.
Whitby goalkeeper Shane Bland saved 2 of Guisborough's penalties and Whitby scored all-but one of theirs to go through to the final of the North Riding Senior Cup for the first time in a number of years.
Attendance: 761.
Manager Nathan Haslam said it was a brilliant night but Whitby did make hard work for themselves:
Blandy lad! 💪 pic.twitter.com/SrXCHhQkX8
— Whitby Town FC (@WhitbyTownFC) March 12, 2024
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