Alcohol was not the cause of the headache, nor was it a hangover from the sight of Ronaldo bearing down on him in the Stade de France less than 24 hours earlier. No, the dilemma was simpler: Calderwood didn't have one of those famous yellow shirts as a memento.
He had come away from Paris and the opening game of the World Cup and forgotten to swap jerseys for the most coveted keepsake in football. It was the only time the defender took his eye off his man all day.
Fortunately, Billy McKinlay came to Calderwood's rescue. The Blackburn Rovers midfielder had managed to trade shirts with Brazil's scorer Cesar Sampaio, despite only being on the field for 11 minutes. "I felt sorry for Colin," McKinlay said, "so I gave him mine. I felt he had played so well for the whole match that he deserved the Brazil shirt more than someone who only came on at the end."
The deal underlines as much as anything that Scotland's all-for-one spirit extends far beyond the touchlines and they will need that on Tuesday night against Norway in what has now become a crucial Group A match in Bordeaux.
After Ronaldo and Rivaldo, comes the more familiar package of Tore Andre Flo and Ole Gunar Solskjaer for Calderwood, and renewing old acquaintances from the Premiership means that phone numbers are as likely to be swapped as jerseys.
Twelve of Egil Olsen's 22-man squad earn their wages in England's top division, two of them goalkeepers, Espen Baardsen and Frode Grodas, who share pegs in Calderwood's dressing-room at White Hart Lane. But familiarity will not breed contempt for the Scot.
"Knowing their players so well helps us, but the situation also helps them," he said. Olsen's devotion to the long ball and his use of the striker-on-stilts, Flo, will have the 33-year-old Scot going back to his days with Mansfield and Swindon. "That was the way a lot of teams played in the lower divisions in those days," he recalled. "Once Wimbledon and Watford got a bit of success with it, everyone cottoned on."
Yet, Calderwood always aspired to higher things. He made his breakthrough at a late age when he moved to Spurs and was not capped until he was almost 30. Now, 30 appearances for his country later, Wednesday's lesson in Paris has given him a further piece of education.
While Christian Gross has preferred to use Calderwood as a midfielder, Craig Brown sees the rugged man from Stranraer as wasted anywhere other than central defence. Such was Calderwood's poise when faced by the running of Ronaldo and Bebeto, that L'Equipe reflected: "He might not win first prize in a contest of elegance, but he controlled Bebeto, was always well- placed and rarely gave away fouls."
That may cause a wry smile among Spurs fans who have not always been taken with Calderwood's defensive capabilities - especially when Flo played against him for Chelsea in the 6-1 humiliation early last season. "He got four," Calderwood said ruefully, "and that had to be the worst moment of last season. I would like to get my own back."
Thankfully for Scotland, Calderwood will have the resilient Colin Hendry alongside him, as well as a more combative midfield. But the dangers of the 6ft 7in Flo remain undiminished. "He is a very good player," Calderwood said, "and a lot better on the ground than people give him credit for. He gave us a real doing with Chelsea and he could be one of the stars of the World Cup."
Solskjaer, replaced at half-time against Morocco, should also be on hand to face Calderwood and the Scot is relishing the task. "They are all good players, and the reason clubs keep buying them is that they have given value for money."
Another who is keenly anticipating the battle in Bordeaux, is Calderwood's benefactor, McKinlay. The midfielder is set to come into Brown's team from the start on an evening which promises to bring earthy challenges to the World Cup.
McKinlay has already won a battle with one Norwegian. He eclipsed Lars Bohinen so thoroughly at Ewood Park that Bohinen left last season to join Derby rather than play second fiddle to the dyed-blond who refuses to bottle anything. "Lars and I joined Rovers on the same day," McKinlay said, "and my move didn't really get any publicity. I felt I was only bought by Ray Harford as a squad player and to be honest if Harford had not left, I would not still be at Blackburn. But once Tony Parkes took over, I got into the team and then Roy Hodgson gave me a more central role and helped my game enormously just by having faith in me."
He is eager to prove his worth to a wider audience on Tuesday. "It's vital for now that we win," he said. "The Norway-Morocco result was a good one for us because we know that if we beat Norway, that puts us in a great position. But it will be very physical, because Norway are a very English-style team."
However, McKinlay admits that the pitch could hardly be any less frenetic than was the bench last Wednesday. "Every time Scotland went over the half-way line, the whole bench was up off its feet urging them on," he said. "We kept getting asked by the cameraman to sit down because we were blocking his view."
By Wednesday, McKinlaywould like to have a clear sight of the second round. He believes it is possible. "The own goal against Brazil summed up Scotland: we are masters of the sob story. But if anything we are in a better position than usual. Everyone thought Norway would beat Morocco, so we're two points ahead of schedule," he said with true Scottish logic.Reuse content