A reshuffled Seadogs line-up were beaten on penalties by Yarm & Eaglescliffe, from four divisions below, on Tuesday night.
Boro were the holders of the North Riding Senior Cup, having lifted the gong three of the last four seasons.
However, the Northern League Second Division visitors went in ahead at half-time.
But it looked as though the Seadogs would steamroller the away side after netting twice in as many minutes at the start of the second period.
Alex Purver's corner swung straight into the roof of the net, then soon after, Will Thornton nodded in for 2-1.
However, the County Durham away side levelled, seven minutes from time for 2-2.
The match went straight to penalties where Jack Waldron fired over the top, for Boro and the away side netted to cap a famous night for them and win 6-5 on spot-kicks to reach the semi-finals.
Here's how it played out on This Is The Coast Extra with commentary from Paddy:
Jono Greening didn't pull any punches speaking to Paddy after the match:
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