In the past year alone the 20-year-old has gone from playing in the third division with Queen's Park to become an established figure with Dundee United, been called up for the Scotland Under-21 side, graduated to the full squad and made his senior international debut, and been voted the 'Young Player of the Year' by his peers.
It seemed as if nothing could possibly go wrong for him. Then came the William Hill Scottish Cup final, the 2-0 loss to St Johnstone the first setback in a career that has only known an upward trajectory. Robertson was not at fault for what transpired that day at Celtic Park but the loss was still a brutal reminder of football's capacity to deliver a sudden blow to the gut when everything seems to be moving along swimmingly.
Robertson's youth and talent mean this will surely not be his only taste of a showpiece event throughout his career - Everton are thought to be keen on taking him to England - but the disappointment several days after the event is still evident. While most of his United team-mates have been left to reflect on what might have been from their swimming pool li-los or beach towels, Robertson has not even had the pleasure yet of the sun on his back to ease his suffering.
That, though, might turn out to be a blessing in disguise. His stellar form has earned him a call-up to the Scotland squad and he could earn his second cap in Wednesday night's friendly against Nigeria in London. The game has extended a season that began for him with a friendly against Union Berlin way back on July 7 and at least now gives him the opportunity to land that happy ending he was denied in the cup final.
"I don't think the disappointment [of losing the cup final] will go away until maybe next season when we're all back together, "admitted the full-back. "It was the quietest bus I've ever been on; the quietest changing room I've ever been in.
"It's tough to reflect on it, because I don't think anyone has got any complaints. St Johnstone were the better team. If we had maybe got a stroke of luck it could have been a whole lot different, but the thing is we shouldn't be relying on luck. We should have been playing better, and if we had played better I believe we should have won it. But we never played as well as we can, and they worked hard and took their chances.
"But at least I'm lucky that I've got the chance to get back on the park this week and hopefully make things right. Some people are finished for the season, so they'll just continue with the disappointment until next season. But I'm away with Scotland and if we can get a positive result that might help to cap off the end of the season.
"I can look back on it all and maybe be proud of what I've done, even though it did end in disappointment. I suppose the only way I can make it end on a high is hopefully getting a good result on Wednesday."
So much has happened so fast for Robertson that there's still a certain novelty attached to being a part of Gordon Strachan's squad following his debut in March's friendly win in Poland. There are few players in the group who would likely leave him quivering in awe and admiration but he admitted he is still getting his head around being asked to perform at this level. His sights, though, are already trained on being involved when the Euro 2016 qualifiers begin in Germany in September.
"You still look up to all these players," he said. "After one time being with them you can't just be comfortable straight away. They're a great bunch of lads and they made me really welcome - and I'm sure it will be the same this time.
"Maybe you're a wee bit more comfortable because you can talk to them and you actually know their faces and not just their names this time. It will be a wee bit easier, I think, but I still look up to them.
"We've been on a good run of form and hopefully we can continue that on Wednesday. And if you impress in training or the game then you would hope that you'd be in with a chance of being in the squad for Germany."