Whitby had the better of this A171 derby but needed a Jack Norton save to claim the Micky Skinner Trophy on penalties.
It was the final friendly before the real stuff starts for these sides, next weekend when Whitby travel to Leek Town in the NPL Premier.
Whitby created plenty of chances against newly-promoted NPL East Guisborough, managed by ex-Blues boss Nathan Haslam.
Left wing-back Stan Hewitt fired wide from distance for the hosts, with Norton saving well, at the other end, at his near post.
Callum Hickman chipped into Guisborough's keeper's hands twice in as many minutes, the second opportunity following great work by Whitby's trialist on the right.
Stuart Rose had a goal ruled out for offside with the same player firing straight at the visiting gloveman around the half hour.
The second period was the usual tepid pre-season fare, Guisborough creating the only chances of note, with Norton again on hand to stop when needed.
The resulting penalty shoot-out saw all spot-kicks converted, except Guisborough's fourth, which was blocked by Norton as Whitby won 5-4.
Whitby Town TV spoke to Blues assistant boss Denny Ingram after the game:
You can catch Whitby's first NPL Premier outing, next Saturday 8th August.
We have live commentary from 3pm on This Is The Coast Extra.


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