The Scarborough & District Saturday League representative side lost 4-2 on penalties after a fiercely competitive 3-3 draw against their Teesside League counterparts at Pickering Town's Mill Lane ground tonight.
Andy Spivey lined up with a 3-5-2 formation, and the early stages looked worrying for the hosts as the Teesside outfit moved the ball around with greater pace and looked dangerous on the front foot.
They took an early lead when poor defending allowed a striker too much space in the six yard box and the ball was nipped past keeper Callum Myers.
Had the Teesside front men been more clinical in the final third, the game could have been done and dusted inside 20 minutes.
A striker headed well wide when well-placed in the six yard box, then Myers saved well when a forward found space yet again.
It could've been even worse had left wing-back Martin Cooper not hacked off the line when Myers was beaten.
Scarborough finally ventured into the Teesside box and Sean Exley was unlucky not to level up when his effort from a tight angle agonisingly trickled wide of the post.
It didn't take the hosts much longer to get on the scoresheet in fortuitous circumstances when Cooper's drive from the edge of the box took a wicked deflection and found the bottom corner after wrong-footing the Teesside keeper.
The sides headed in level at the break, with the home side probably the happier of the two.
Scarborough improved after the break but lost Exley to a hamstring injury, and he was replaced by West Pier's Neil Thomas.
The hosts took the lead when Hunmanby defender Leigh Franks, who was having an exceptional game at the heart of Scarborough's back three, ghosted in at the back post to guide Cooper's pinpoint free-kick into the back of the net.
A heated spell followed as the away side started to lose their discipline after a series of decisions went against them.
Their anger abated temporarily when they got back on level terms, Myers spilling an effort from close-range and a striker followed up sharply to ram home for 2-2.
The Teesside contingent were again left frustrated when Scarborough took a 3-2 lead in pretty much similar circumstances to their second.
Cooper whipped in another well-directed free-kick and Will Jenkinson bundled the ball over the line to put the hosts back in front.
Franks had been in imperious form at the back, marshalling the hosts' defence, but he was forced off with a suspected broken arm after making a superb last ditch sliding challenge.
He was replaced by Filey's James Jenkinson, who was caught cold within moments of arriving on the pitch as a Teesside man turned him in the box and laid off to a teammate who tapped in for 3-3.
Franks was taken straight to hospital after the injury, and there was further need for a defensive re-shuffle when Newlands' Ricky Nock was forced off, replaced by Pier's Tommy Barker.
Neither side could find a way through and the contest went straight to penalties.
Myers couldn't keep out any of the Teesside pens, while Darren Clough, who had impressed throughout for Scarborough, missed with a tame penalty before Gary Thomas also saw a tame spot-kick saved.
Rep Team: Myers, Nock, Franks, G Thomas, Garnett, Cooper, Gallagher, W Jenkinson, Craig, Exley, Clough. Subs: J Jenkinson, Barker, N Thomas, Sheader.
SN Star Man: Leigh Franks was solid at the heart of the Scarborough defence before he departed with a suspected broken arm, while Darren Clough and Martin Cooper also impressed.