The latter success represents the last time Scotland beat England at Hampden and McLeish played a key role in that victory.
Yet, although the countries have met 113 times since taking part in the world’s first international football match in Partick 145 years ago, the former Scotland manager argues that the clash with Gareth Southgate’s side in nine days’ time eclipses every one that has gone before in terms of the significance of the outcome for the home side.
At the halfway stage, the Scots are currently fourth in Group F of the qualifying competition for next year’s World Cup finals in Russia, six points behind leaders England, two adrift of Slovakia and one away from Slovenia, who were beaten at Hampden in March.
While the countries have faced each other in a major championship before – host nation England winning 2-0 at Euro 96 – McLeish argues that the World Cup outranks all other tournaments.
And, in the context of Scotland boss Gordon Strachan once again needing to prevail in order to keep hopes of progressing from the group alive, he states that the latest encounter is, unequivocally, the most important one yet.
“At this part of our history, it is,” he claimed. “That’s not to put more pressure on the players; they’re playing at good levels and so mentality shouldn’t be a problem. This is a big occasion and, because it’s England, they’ll roll the sleeves up that wee bit further.
“This one coming up is even more important than the Home Internationals, as it was when I played. This is qualification for the major tournament. If Gordon can win this then we’ll all be in his debt.”
McLeish still fondly recalls how he played a key role the last time Scotland beat England at Hampden, in 1985.
“I put Jim Bett clear and it was from Jim’s cross that Richard Gough scored,” he said. “We lap it up whenever we beat England. It’s a special game – it always feels like a cup final.”
His favourite memory of the fixture, though, was when he shut out Ron Greenwood’s side at Wembley, with Nottingham Forest winger John Robertson scoring the only goal from a penalty awarded when Bryan Robson brought down Steve Archibald.
“The pitch was energy-sapping and that’s because of the aura of the arena,” he said. “I’d played at Hampden enough times to not be overawed by playing there and we were determined not to be overawed by Wembley.
“Willie Miller and I were playing against Peter Withe [of English champions Aston Villa] and [Nottingham Forest’s European Cup winner] Trevor Francis and we coped pretty well but, at the end of the game, I remember my feet were all blistered.
“It wasn’t new boots, it was just the surface; you felt as though you’d run a marathon. The English media were really dismissive before the game, they were saying they’d run riot against the two Aberdeen centre-backs.
“Danny McGrain was beside us and he told us not to play offside – he said he didn’t really know how to do it! He just wanted to defend [his flank] – I couldn’t believe Danny had never played offside but the tactics worked really well for us.”
Tottenham Hotspur striker Harry Kane, the Premier League’s leading goalscorer for the past two seasons, is the biggest danger to the Scots, according to McLeish.
“He’s an absolute monster of a player, fantastic,” he said. “He reminds me of Martin Chivers, from the old black-and-white telly days of big strong English centre-forwards. He fits that kind of bill – a skilful, powerful runner, he’s just about got the lot.
“We’ve got to stop him but there are others we have to stop. I’ve seen a lot of the teams in London this season and Dele Alli’s been the most creative player in the league.”