Both of Gordon’s triumphs in football’s nerve-shredding tie-breaker have come in this competition as a Hearts goalkeeper. The first gave his boyhood heroes a significant advantage in the 2006 Scottish Cup final against Gretna as he saved from ex-Hibs man Derek Townsley before Gavin Skelton blasted off the crossbar to seal the win.
His latest victim was Livingston defender Ayo Obileye. Already reeling from missing a crucial penalty in the midweek draw with Ross County in the cinch Premiership, Obileye had his effort held by the Gorgie custodian. This saw Hearts through to the next round after John Souttar, Peter Haring, Ben Woodburn and Ellis Simms made no mistake, while Cristian Montano missed for Livi following 120 goalless minutes.
Obileye now joins Townsley, Gabriel Agbonlahor, Nicky Clark and Ryan Christie in an eclectic list of players who’ve had a penalty repelled by the current Scotland No.1 during a shoot-out. Impressively, he’s managed one stop on each occasion.
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After the Gretna win, Gordon was on the losing side to Aston Villa in a Carling Cup match for Sunderland in 2009; against Rangers in the 2016 Scottish Cup semi-final while at Celtic, and against his former club in the 2020 Scottish Cup final when he denied Christie with the third kick but watched on as Stephen Kingsley and Craig Wighton missed, allowing Kristoffer Ajer to blast home for the win.
Though any supporter would wish to avoid the anxiety, Gordon believes Hearts may now have some added confidence if it comes down to penalties again in this year’s tournament.
“That’s only my second win out of five. It was good to help out,” he said. “I normally seem to be able to get one out of the five, so if I can do that and then if the guys can score their penalties then I give the team a chance.
“Every penalty shootout I’ve been in I’ve managed to save one, so then it’s up to the other guys to hit the target and they were excellent. They stepped up and slotted their penalties away.
"We didn’t manage to pull it off that day [against Celtic], but everybody stepped up and scored today. I managed to keep one out, so that was us hopefully putting that behind us and now if we do have another penalty shootout, then we’ve got good memories to fall back on from this one.”
Gordon later revealed facing Obileye from the spot against Queen of the South in the Championship last season gave him a bit of prior knowledge, though he doesn’t believe too much in studying what opponents like to do.
“It was a similar penalty today. I had one or two bits of information, but any player can change their side or do whatever, so it’s a bit of cat and mouse really, you don’t always want to look too much into what players have done before.
“They know you’re looking at that, so they might change it, so there’s all sorts of little games going on, so you just hope you pick the right side more often than not.”