If the midfielder's path to stardom has been steady rather than remarkable since then, thankfully the Scotland manager isn't the type to bear a grudge. Strachan could hardly fail to be impressed by the manner in which Bryson has scored five goals in three weeks from an advanced midfield role at Derby County and has been equally taken by the way he has acquitted himself when he was called into the squad for last month's match against Macedonia.
That is why, having made his Scotland debut under Craig Levein against the Faroe Islands, he is in the mix to deputise for Shaun Maloney - also in the opposing line-up that fateful day - in that crucial role behind the striker as Scotland bring down the curtain on an eventful qualifying campaign against Croatia in nine days' time.
"I've always disliked him since then, to be honest with you!" joked Strachan. "But, no, he has done well. I like to see players who, when they're training or playing, say 'listen, I've got to make every day count'. I've got to impress the manager, impress my team-mates, be the best man on the pitch at training, be the best man on the pitch in a game. I like that."
Places are still up for grabs in the team which will take to the field against the Croats - a side scalped by Strachan's Scotland in Zagreb in May - but already the contours are taking shape. The suspension of Steven Whittaker provides Lee Wallace of Rangers with a merited chance to prove he can step up from SPFL League One to international level at left-back. In the central area, it would seem unwise to disrupt the centre-half pairing Grant Hanley and Russell Martin, with Alan Hutton - despite his lack of games at Aston Villa - still looking the best available option at right-back.
In midfield, there is a welcome return for the versatile James Morrison, and there were also words of support for Charlie Adam, who has at least been playing regularly at Stoke City, even if finding the correct role to include him in a Scotland side remains a puzzle. "Well, he's getting a game," said Strachan. "That's the most important thing, because when he turned up when I first took over he wasn't getting games."
Bryson's goals at Derby were unable to prevent manager Nigel Clough being replaced by Steve McClaren, with Strachan's successor at Middlesbrough, Tony Mowbray - now the longest-serving manager in the Championship - also under pressure for his job. The Scotland boss feels the short shelf life of managers in that division is simply a fact of footballing life.
"We're all getting to know now that you can lose your job after nine months or a year," he said. "That's the way it is. The bonus to get up is fantastic for the successful club, but it's the same guys who seem to be on the circuit. He got sacked three months ago and he's got another job and you think: 'what happened there?'"