Aberdeen goalkeeper Jim Leighton remembers telling a few people in the week running up to the 2000 Scottish Cup final that he was going to be the very last soul off the Hampden pitch.

“Apparently, I lasted 90 seconds before Rod Wallace hit me, so sometimes you can put your size 10s in your mouth quite easily,” the former Scotland keeper laughs.

It was to be the Leighton’s last hurrah in a distinguished career. What transpired, a broken jaw forcing the then 41-year-old out of the showpiece against title winners Rangers after three minutes and, with no goalkeeper among the three substitutes, meant striker Robbie Winters would take his place between the sticks.

Twenty years to the day since it happened, BBC Scotland recalls one of the most bizarre moments in Scottish football history.

‘I said we needed a goalie on the bench’

In 2000 and then under the stewardship of the eccentric Dane Ebbe Skovdahl, Aberdeen had finished bottom of the Scottish Premier League but had also managed to reach the League Cup final, which they lost to Celtic. A star-studded Rangers, having won the treble the season before under Dick Advocaat, had wrapped up back-to-back titles and were aiming for the double.

Leighton, who was doubling up as Aberdeen’s goalkeeping coach, recalls a conversation with Skovdahl in the build-up which, with the benefit of 20 years of hindsight, seems laughable.

“I said: ‘Look I know what you’re going to say to me, but I wouldn’t be doing my job as a goalie coach if I didn’t say my piece – I think we should have a goalie on the bench. What happens if I get sent off after five minutes and we’ve not got a goalie on the bench? The game’s dead’,” he said.

“He said: ‘That’s the way that I think gives me the best chance to win the game’. That’s what Dick Advocaat had done as well. It worked for them, it didn’t work for us.”

Winters also speaks of some foreshadowing in the weeks before he found himself in the spotlight.

“It had been mentioned by Ebbe a couple of weeks before to everybody,” Winters recalled to The Herald in 2017. “‘Would anyone like to go in if something happened?’. There were only three subs at the time so I put my hand up no problem. It is one of those things that you just do, but you never thought it would come true.”

‘Any chance you get, have a pop’

But come true it did. Rangers striker Wallace stretched to try to turn in Andrei Kanchelskis’ cross and caught Leighton, who bravely threw himself on the ball. The Aberdeen keeper was down for about seven minutes, before eventually being led off.

“You’re thinking, ‘they’re in trouble’,” says Billy Dodds, who played and scored for Rangers that day.

“Jim’s in trouble first and foremost, you’re hoping he’s alright. But if he goes off, who are they going to put in goals? That was the first question. There’s nae goalies!”

Jim Leighton is stretchered off just a handful of minutes into the game

Enter Winters, who jogged on rather comically wearing reserve goalkeeper Ryan Esson’s top and looking like, in his own words, “a 16-year-old” and “little boy lost”. “It works the other way. If we put on an outfield strip, it doesn’t look right,” Leighton laughs. The irony was that Esson was fit and available having warmed Leighton up, before getting changed into his suit and taking his seat in the South Stand.

BBC co-commentator and former Rangers midfielder Gordon Smith remarked that there was now “even less pressure” on Aberdeen and, for half an hour or so, they stood firm. Rangers barely tested Winters, with the make-shift keeper managing to hold a Jorg Albertz strike from distance and, much more impressively, tip a close-range volley from Wallace on to the crossbar.

“For the first half hour we were poor, didn’t even really trouble Robbie after Jim got carried off,” Dodds said. “You could feel the fans starting to get a wee bit restless.

“The boys were saying it themselves. ‘Any chance you get in a decent shooting position, have a pop’. But Robbie did pretty well, he had a few good saves. He was pretty competent.”

Taking stick in a taxi

The honeymoon period did not last long, though. A quick free-kick on 35 minutes allowed Giovanni van Bronckhorst to volley into the back of the net. The strike was powerful, but straight at Winters and one Leighton would have fancied saving.

Then, three goals in four early second-half minutes from Tony Vidmar, Dodds, and then Jorg Albertz threatened to make it a cricket score. None of the goals could really be attributed to poor goalkeeping, and indeed Winters pulled off a spectacular save to deny Dodds late in the game.

Meanwhile, Leighton was in the bowels of Hampden, knowing he would not play competitively again.

“The ambulance took me up to the hospital, it took me a while. I had to go to Bon Secours [another hospital] to get an x-ray on a machine that went around me,” Leighton recalls.

Winters, alongside Aberdeen boss Ebbe Skovdahl, preparing to come on for Leighton

“So, at the end of the game I’m sitting in a taxi with my strip on in amongst all the Rangers fans trying to get to Bon Secours and they’re all giving me dog’s abuse, which is exactly what I was needing!

“By the end of the game somebody had come and told me what the score was. See to be honest, there was a gulf between the two teams anyway. I’d played against Rangers that season and I think they’d scored five and six against me.”

Rangers had no replacement goalkeeper that afternoon either, but Stefan Klos managed to keep himself out of trouble. The rules were changed after the final to allow for five substitutes, with clubs compelled to put a goalkeeper on the bench.

Winters went on to finish a productive four-year spell at Aberdeen where he was tasked with scoring rather than saving goals. But this bizarre moment in Scottish football history is often the one he is remembered for, even after his title success in Norway with Brann Bergen.

“I think the Aberdeen fans accepted it,” he told The Herald. “I spoke to a lot of them after the game, we had a big dinner that night up in Aberdeen and I was star man.

“It was a good laugh afterwards but you wanted to do well for the club and obviously win the cup but it wasn’t to be. The circumstances kind of spoiled it.”