On the eve of Scotland’s third UEFA Nations League match in North Macedonia, the captain stands on the verge of history.
Poised to earn his 100th cap for Scotland and move closer to surpassing the legendary Kenny Dalglish, Andy Robertson has experienced it all. From Mount Florida to Munich, from Brussels to Boston, his journey has mirrored the steady rise of the national team over the past decade.
As he prepares for a potential century of appearances in Skopje on Saturday evening, it is worth reflecting on the key moments that helped shape one of Scotland’s greatest modern players.
Poland 0-1 Scotland (2014)
What began as a forgettable international friendly became an unforgettable occasion for Robertson. Introduced in place of Barry Bannan with 23 minutes remaining, the then 19-year-old made his Scotland debut under Gordon Strachan in Warsaw.
Scott Brown’s fierce 19-yard strike past Wojciech Szczęsny secured a narrow victory for Scotland, but the night belonged to the young left-back. Having only recently completed his remarkable rise from Queen’s Park to full-time professional football with Dundee United, his first appearance on the international stage marked another significant milestone in an already impressive ascent.
Speaking after the match, Robertson expressed his delight at making his debut and hoped there would be “many Scotland squads to come.” More than a decade later, as he stands on the brink of his 100th cap, it is fair to say he got that prediction right.
Scotland 1-3 England (Nov 2014)
Since his debut in Warsaw, Robertson’s impressive form at Dundee United earned him a £2.85 million move to Hull City. By the time of his fifth international cap, and fourth competitive appearance, he was thrown into the cauldron of Celtic Park to face the Auld Enemy.
Robertson was no stranger to being thrown in at the deep end, but England’s superior quality and experience proved decisive in the Euro 2016 qualifier in Glasgow. Goals from Alex Oxlade-Chamberlain and a brace from Wayne Rooney left Scotland reeling, with manager Gordon Strachan later admitting his side had been “spooked” by the visitors.
There were still personal memories to be made for Robertson. His close-range finish in the 83rd minute gave Scotland hope at 2-1, but the comeback would ultimately fall short. The defender had earlier been involved in England’s second goal when his skewed clearance fell kindly to Rooney, who made no mistake.
While the result represented a setback for the national team, it marked another important step in Robertson’s development as his remarkable rise continued.
Scotland 0-4 Belgium – (Sept 2018)
A disappointing defeat to a classy Belgium side marked Robertson’s first match as captain of the national team. The decision, made by manager Alex McLeish, was the beginning of what has since become a remarkable leadership tenure. Robertson has now captained Scotland on 77 occasions, a national record that places him comfortably ahead of figures such as Graeme Souness, Gary McAllister, and Billy Bremner.
Despite the honour of leading his country, Scotland found themselves outclassed by their opponents. Belgium controlled the match from start to finish, with captain Eden Hazard pulling the strings throughout. Romelu Lukaku opened the scoring after John McGinn was dispossessed in midfield, while Michy Batshuayi capitalised on defensive errors as the visitors delivered a footballing lesson to the Scots.
The defeat marked a fourth loss in five matches under McLeish as Scotland continued to endure a difficult period.
For Robertson, however, the occasion signalled the start of an enduring spell as Scotland captain. While the result itself offered little cause for celebration, it marked the beginning of a leadership journey that would span more than eight years, with far greater success awaiting both Robertson and the Tartan Army in the years to come.
Serbia 1(4)- 1(5) Scotland (Nov 2020)
Robertson led his side to Serbia, with the single goal of sending Scotland to a major tournament for the 23 long, painful years. After navigating a playoff semi-final on penalties at Hampden, Scotland faced another marathon in Belgrade. In the midst of COVID-19, the cold, empty stadium added another layer of tension for the millions watching at home, and the team put the Tartan Army through another torturous evening.
Robertson led his side for the full 120 minutes. Ryan Christie turned on the edge of the box to squeeze a left-footed strike past the stretching Predrag Rajković. With seconds to play however, Luka Jovic headed the sides into extra time.
Penalties followed, and after a perfect 5 out of 5 from the Scots, and a low save from the heroic David Marshall qualification was sealed, for the nation it was 23 years of heartache over, and for Robertson, the chance to captain his side on the major tournament stage.
Scotland 2-0 Spain – (March 2023)
Robertson featured in six of Scotland’s eight Euro 2024 qualifiers, anchoring a spellbinding campaign that opened with five straight victories and secured automatic qualification for Germany ahead of a favoured Norway side.
While the campaign boasted several defining moments, including the miracle in Oslo, none were more iconic than the famous 2-0 victory over Spain at Hampden Park. Scott McTominay crashed home a goal in each half, delivering a result that, three years on, remains Spain’s last competitive defeat.
Robertson put in a trademark performance, flying up the left flank with Kieran Tierney offering relentless support behind him. Capitalising on a slip from Pedro Porro, Robertson picked out McTominay for one of his eleven international assists.
After years of enduring dismal home nights, such as the Belgium defeat, this triumph was a night to cherish for the Tartan Army, with Robertson, once again, right at the heart of it.
Scotland 0-1 Hungary (June 2024)
After cruising through qualification, Scotland faced familiar heartache at the tournament proper. Leading his side at a second straight Euros, captain Andy Robertson started all three Group A games as Scotland failed to reach the knockout stages.
A heavy 5-1 defeat to Germany in Munich put the Scots on the back foot, but a resilient 1-1 draw with Switzerland kept their hopes alive. The equation in Stuttgart was simple: beat Hungary, and history awaited.
In a tense, tactical contest, clear chances were scarce. Scotland pressed in the second half and made strong claims for a penalty when Stuart Armstrong fell under pressure in the box, but the referee waved play on.
Disaster struck deep into stoppage time. With Robertson having been substituted in the 89th minute for attacker Lewis Morgan, Hungary hit Scotland on the break in the 100th minute to seal their fate. The heartbreak was complete, leaving the Tartan Army waiting once more for that elusive knockout berth.
Scotland 1-0 Haiti (June 2026)
Winning his 95th cap, Robertson once again led his national team out at a major tournament. Scotland had thrillingly topped their group, securing qualification with a heroic 4-2 victory over Denmark to make Robertson the first Scottish captain at a World Cup since Colin Hendry in 1998.
Twenty-eight years after Scotland’s last World Cup appearance, Robertson stood proudly at the helm. A strike from John McGinn on the half-hour mark earned the Scots a 1-0 win, their first victory at the tournament in 36 years.
It may not have been the prettier of performances, but Robertson marshalled his side with composure, showing just how far he had progressed since making his debut back in 2014.
Andy Robertson’s path to 100 caps is a testament to his resilience and leadership in a Scotland shirt. He has taken the Tartan Army through the darkest nights and guided them to light on the global stage, solidifying his legacy as one of Scotland’s greatest modern icons.
Reaching a century of caps in Skopje is a monumental milestone. Congratulations to Andy Robertson – a true leader, a legend of Scottish football, and now a Scotland Centurion.
