He has suffered the pain of World Cup and European Championship qualifier exits.
So Callum Davidson reckons it’s high time Lady Luck smiled on Scotland.
The St Johnstone manager played in the 1-0 1999 Wembley win over a star-studded England side featuring Alan Shearer, David Beckham, Michael Owen and Tony Adams.
But Craig Brown’s side agonisingly missed out 2-1 on aggregate in the two-legged tie for a place at Euro 2000 in the Netherlands and Belgium.
And three years ago Davidson was a member of Gordon Strachan’s backroom team which drew 2-2 with the Auld Enemy.
Harry Kane’s stoppage time leveller left Scotland’s World Cup qualification hopes in tatters after Leigh Griffiths had blasted them into a 2-1 lead with two stunning free-kick strikes.
Over two decades have passed since Davidson was on the bench at Hampden when a Paul Scholes brace put Kevin Keegan’s England in the driving seat.
He then figured in the team which came agonisingly close to overturning the deficit after Don Hutchison’s goal beneath the Twin Towers.
“Back then we had qualified for so many tournaments, including the World Cup in France the year before,” recalled former Leicester City and Blackburn Rovers full-back Davidson.
“I don’t think any of us thought the wait for another one would be so long.
“Losing to your biggest rivals in a play-off match is the worst thing ever.
“But for me looking back I still have the memory of playing and winning at Wembley.
“As a Scotsman that is fantastic, even if there were mixed emotions after the game.
“Christian Dailly had a chance near the end to equalise but he probably caught it too well and it was a great save by David Seaman.
“It would have been interesting if it had gone to extra time because I was cramping up after 75 minutes. I don’t know if I’d have lasted much longer.”
Fast forward to 2017 and Davidson suffered more international heartache in a group clash.
“That was a hard one being assistant manager at the time,” he said.
“The Griffiths free-kicks were spectacular and the crowd noise that day at Hampden will live with me for the rest of my life.
“Then Kane got that late equaliser. That sums-up Scotland but it would be great if we can change all that against Serbia.
“Hopefully we can put in a performance and get the result needed to give the nation something to get really excited about.
“I think we are overdue a result in one of these qualifiers.”
Steve Clarke’s men can hand Scottish football a huge boost if they claim a spot at next summer’s Euro finals by seeing off the Serbs.
And Davidson isn’t bothered how they do it in Belgrade.
He said: “I’d settle for a win on penalties if that’s what it takes. I’d take anything to go through.
“It is going to be a real tough game. They are a top team and we shouldn’t under-estimate them.
“But we have given ourselves a real chance.
“It would great for Scottish football to make the finals next summer.
“You look at players coming into the squad from Hibs and Aberdeen. The league is producing some very good young players.
“Hopefully Steve can get the right balance to the team and get us performing to a high level.”