YORK City were dumped out of the North Riding Senior Cup 4-3 on penalties at Guisborough Town.
Despite successful spot kicks by Bradley Fewster, Callum Rzonca and Taron Hare, along with a fine save from Michael Ingham, George Swan hit the bar and Josh Carson a post as the Northern League title contenders progressed to the semi-finals.
Steven Smith, Dan McWilliams, Liam McPhillips all converted for the hosts, while Ingham saved well from Danny Earl, but right-back Jonathan Helm kept his nerve to settle the tie.
The score after 90 minutes had been deadlocked at 0-0 following s shot-shy City performance.
Ex-Scotland international Derek Riordan completed 70 minutes in his first outing for the Minstermen, while fellow first-team squad members Ingham, Carson, Fewster, Ntumba Massanka, Swan, Rzonca and Hare were given full run-outs.
The rest of the squad was made up of youth-team scholars with midfielder Tyler Walton impressing the most.
A poor first half saw Fewster win an early free kick for City after his positive run was ended cynically by home captain Leon Carling.
But Riordan’s 30-yard drive was safely gathered by Guisborough keeper Nick Liversedge after it deflected off the visitors’ wall.
Riordan, operating just behind the Minstermen’s front two, also tried his luck from the edge of the box after Carson was fouled following a forward surge but his attempt was blocked and he then missed his kick when the ball rebounded to him.
On 18 minutes, Rzonca also forced Liversedge into a near-post save, but Guisborough missed the best chance of the first period when Earl somehow missed from two yards at the far post following a left-wing raid by the hosts.
At the other end, Massanka’s weak shot failed to trouble the Priorymen’s keeper before youth-team left-back Sam Jefferson was carried off following a nasty challenge.
Further hopeful efforts from Rzonca (twice), Walton, Massanka and Fewster failed to break the deadlock before the interval.
In the second half, Guisborough started brightly with Connor Smith heading just wide from eight yards.
Riordan then broke clear on goal for the Minstermen but was denied by Liversedge’s outstretched left leg.
City keeper Ingham, meanwhile, smothered an Earl effort on 69 minutes with Hare, who was switched to left back following Jefferson’s injuty, forcing a near-post save moments later.
Curtis Round also went on to lift a promising edge-of-the-box opportunity for the north-east amateurs as the game headed for penalties.
City: Ingham, Hare, Swan, Brettel, Jefferson (Freer, 25), Rzonca, Carson, Walton, Riordan (Fielding, 71), Massanka, Fewster.