Elgin City exited the SPFL Trust Trophy after 10-man Clyde triumphed on penalties at Borough Briggs.
The sides could not be separated during the goalless 90 minutes, with the visitors playing the final half hour a man down following Andrew Rodden’s red card.
League One outfit Clyde triumphed 4-2 on spot-kicks however, after Darryl McHardy and Fin Allen saw their efforts saved.
Elgin were able to call upon skipper Matthew Cooper for the first time since October 1, replacing Owen Cairns at right back, while Chris Antoniazzi was drafted in for Tom Findlay.
City created the first chance inside the opening two minutes when Brian Cameron helped the ball through to Kane Hester, with Elgin’s leading scorer seeing two efforts foiled by the Clyde backline.
Clyde’s first meaningful glimpse of goal came on 16 minutes when Jordan Allan evaded the attentions of Jake Dolzanski, but drilled his effort wide of the far post.
Chances were few and far between at both ends in the first half, however a ball over the top set up another fine chance for Allan who once again dragged his effort wide on 39 minutes.
Gavin Price made a half-time change, with Dylan Lawrence replacing Antoniazzi.
The visitors were reduced to 10 men on 57 minutes, when Rodden was shown a straight red card for an over robust challenge on Cooper. Although it left the returning Elgin captain in severe pain, he was able to shake it off to continue.
Clyde still posed a threat however, with Barry Cuddihy seeing an effort held at the second attempt by Thomas McHale.
The Elgin goalkeeper was called upon again shortly afterwards, getting down to beat away a half volleyed effort from substitute Oliver McDonald.
Elgin stepped up their efforts to make the numerical advantage, with Russell Dingwall thwarted by a saving challenge by Brian McLean after being played through by Lawrence.
Hester was next to threaten on 82 minutes, as he smashed an effort into the side netting, while substitute Fin Allen forced Neil Parry to tip around the post shortly afterwards.
The best late chances fell to Dingwall, with the midfielder twice steering wide as he bore down on goal, albeit with the help of a deflection on the second occasion, however it was the Bully Wee who ultimately progressed to the quarter-finals.
