Suddenly it is all happening for a player who has turned out at Hartlepool as often as at Liverpool. Barely a fortnight after representing Scotland in Russia, Calderwood will be at the heart of Tottenham Hotspur's defence in Sunday's semi-final against Everton at Elland Road. More than anyone, his change of fortune mirrors Spurs' transformation under the managership of Gerry Francis.
The irony is not lost on Calderwood. As one who was with Ossie Ardiles at Swindon, he expected to be purged from White Hart Lane once the Argentinian was ousted. Instead, the change was the making of him. No longer left exposed by a Utopian attacking formation, he showed the coolness on the Premiership stage that earned him the nickname "Fridge" at his previous club.
"Gerry dragged me out of the dungeons," he admitted. "I felt for Ossie and wondered if perhaps I could have done more, but we had no consistency. Playing five forwards worked every now and then, and we looked brilliant when it did. But some days it was murder at the back.
"Spurs fans used to tell me they'd sacrifice `the Tottenham way' if it meant winning more games. Now we seem to have struck a good balance between the two."
Often described as a late developer, Calderwood prefers the theory that he has found the right role in a more suitable system. Mysteriously for one who graced midfield, Ardiles seemed to view that area as important only in so far as it related to all-out attack, a philosophy which often left his defenders vulnerable to opponents running at them.
Francis, seeking to protect his centre-backs, introduced David Howells as midfield anchor, as well as giving the other players defensive duties. Calderwood and Gary Mabbutt, the Spurs captain, have thrived within this revised structure. Notwithstanding last Sunday's blip at Southampton, Spurs look tighter than at any time since the partnership between Mabbutt and Richard Gough helped them to the 1987 final.
In the same way as the new tactics did not work instantly - they were three down to Aston Villa early in Francis's first match before losing 4-3 - so Calderwood's career suffered a false start. After leaving his Stranraer home to be an apprentice with Mansfield - "No one else even offered me a trial" - he made his debut as a 17-year-old.
However, the club had failed to register him, and were docked two points. Like an over-zealous man-marker, sleaze continued to pursue him. In 1990, four years after moving to Swindon, he was caught in the crossfire between club and taxman. No sooner had he decamped to Spurs, than they were peppered with penalties for financial irregularities of their own.
During the Swindon saga, Calderwood was actually arrested for allegedly defrauding the Inland Revenue by accepting a "bung" to sign from Mansfield. He was cleared, but Swindon, having won promotion to the former First Division with Ardiles in charge, were demoted to the Third Division as punishment for maladministration.
"We were told the club would probably get a fine, so the thought of going down never entered our minds," Calderwood recalled. "One Friday, we had some friends round for a meal. We were about to sit down when a reporter rang to say we'd been relegated. The food never got eaten."
On appeal, Swindon stayed in the old Second Division, and with Calderwood as captain eventually completed a seven-season rise from the Fourth to the Premier League under Glenn Hoddle. From Lou Macari, Calderwood learned the value of rest and fitness. Ardiles and Hoddle brought out his constructive side, confirming the logic behind his £1.25m transfer to the club where they once performed in magical tandem.
Last season, his first with Spurs, was not a success for either himself or the team. He was no Neil Ruddock, the critics complained, and by May, Ardiles had agreed to sell him to Macari at Celtic. Before he could sign, Macari was sacked, so Calderwood stayed. "It wasn't exactly a vote of confidence," he said.
Before the managerial upheaval that followed the Coca-Cola Cup collapse at Notts County, where he suffered the indignity of being substituted at half-time, there was talk of his rejoining Swindon. Now he is playing the best football of his life, an impression confirmed in Moscow, and is one win from the final of a competition from which Spurs were originally excluded.
"The Cup ban was never a big thing with the players," Calderwood said. "What really worried us was the 12-point penalty in the League. Even when it was cut to six, it only gave us a fighting chance. People assume it'll be a Tottenham v Manchester United final. I can assure you none of us thinks that, and the same will be true at Everton."
Yet circumstances, the latest being Duncan Ferguson's suspension, keep conspiring to make it look like Spurs' year. "His absence has got to be a boost for us, because he's been a real player for them. But Paul Rideout could be back, and Daniel Amokachi has done well recently."
One might expect a defender regularly tangling with Jrgen Klinsmann and Teddy Sheringham in training to have no qualms about facing such players; either that or have his confidence shot. "It's not too bad," he revealed. "We usually play the old ones against the young ones, so I get to have them on my side."
Increasingly, Spurs' celebrated strikers probably share his satisfaction with their practice arrangements. For Calderwood, hoping to see the light at the end of the Wembley tunnel after a patient journey from obscurity, that is recognition indeed.Reuse content