The 20 year-old's career path to date has been like a throwback to a different era; player released by first club (Celtic), signs for lowly amateur side (Queen's Park), earns move to SPFL Premiership club (Dundee United), makes international debut (for Scotland), then makes big-money move to the Barclays Premier League (with Hull City).
What makes it even more astonishing is that Robertson has achieved all of that within the space of just three years. Even Roy Race never managed so much, so quickly.
Robertson, though, seems quite matter-of-fact about it all. Not blase or nonchalant but similarly not overwhelmed by how far he has come in a relatively short period of time. If he lies awake at night, wracked by self-doubt about whether he is good enough for this level, then it is not something he is of a mind to share at this juncture. But his easygoing, self-deprecating manner and the insistence that he isn't "anywhere near the complete article" seem to suggest he has somehow been able to maintain a sense of equanimity despite the sharpest career rise since the Wolf of Wall Street.
He has taken it all in its stride simply by not thinking about too often or too deeply. There may come a point when he finds himself in a state of reflection, mulling over the fact that 16 months ago he was still playing in the Scottish fourth tier, but for now he is just enjoying the journey. A question about whether he has now hit the big time provokes the most emphatic of denials. "No, never," he replies, looking almost horrified at the suggestion. "It is just the way I am - I never think like that.
"I am still the same person I was at school two years ago. There is no point in changing. I don't look back. I just try to take everything in my stride. I have done a pretty good job there so far and I just want to continue that."
His singing has improved at the same rate as his football. The old ritual of a new recruit having to perform a song in front of his new team-mates is still going strong and, having signed for three clubs and been called up for international duty all in the last few years, Robertson has had plenty of practice.
"I've done it four times in three years now, that's the only downside to moving clubs," he adds with a laugh. "The song wasn't what you'd expect - it was Kenny Rogers' The Gambler. It's a nice easy song and the boys all clapped along when I got to the second verse so it wasn't too bad."
Then there was the novelty of seeing himself on television of a Saturday night. "The people who sadly stay in on a Saturday - and I include myself in there - look forward to Match of the Day," he admits. "That was a wee bit weird for my family and friends."
Robertson has settled in well at Hull, and started all three of their Premier League matches. Even following Saturday's defeat to Aston Villa his performance was being held up as the one bright spot on an otherwise dark day.
"It is another step up," he added. "It is a quicker tempo and there are a lot of things I still need to work on. We played Stoke City last week and played 80 minutes with 10 men and it was the hardest game I have ever played in, just with the physical demands. I saw in that game that there is a big difference.
"I don't think I am anywhere near the complete article that I feel I can be. Everything I get praised for I can still work on and get better.
"There is no point in getting nervous. I get a few butterflies in my stomach but it isn't really nerves but things that will help your game."
Such a stoic attitude will come in handy this weekend. Robertson only has two caps to his name but seems certain to start against the world champions Germany in Scotland's opening Euro 2016 qualifying match in Dortmund. "You want to test yourself against the best but we have come a long way," he added.
"We are a lot more confident than we would have been 18 months ago and we are all looking forward to it. We'll just stick to the way we want to play and see how it goes."