'Robbo' is the club's all-time leading scorer with 214 goals spanning 18 years across two spells, but his only winners' medal came as an unused substitute in the 1998 Scottish Cup final, his last match for the club.
It came after several near misses for both Hearts and their talismanic striker, including the agonising defeat at Dens Park in the final mach of the 1985-86 season which cost the club the Scottish Premier Division title.
Hearts finished league runners-up on three occasions during Robertson's time at the club, and lost three finals, twice in the Scottish Cup and once in the League Cup.
Speaking ahead of the release of his autobiography on October 28, Robertson admitted the 1986 defeat to Albert Kidd’s Dundee was the toughest part to put into words.
“It was the one section in the book that took a long time,” the 57-year-old told The Guardian. “It got to Dens and I wondered how on earth to approach it. The hardest bit was that emotional aspect, trying to explain how we all felt after that game. Had we seen the league out I have absolutely no doubt we would have beaten Aberdeen.”
Hearts lost 3-0 to the Dons in the Scottish Cup final at Hampden Park a week later. It would take another 12 years for Robertson to get his winners' medal, and for the club to end a trophy drought stretching back to 1962.
“Despite the reinvigoration of the club, we left a lot of chances out there. I lost in 10 or 11 semi-finals as well as three cup finals. The opportunities we missed as a team and I missed as an individual were huge.”
The current Hearts side are protecting the only remaining unbeaten record in the Scottish Premiership when they travel to Ibrox this Saturday to face a Rangers side just a point ahead of them at the top of the table.
Robertson, now Inverness Caledonian Thistle sporting director, detailed how he almost joined the Glasgow club prior to rejoining Hearts following a short-lived spell at Newcastle United in 1988.
"Rangers came in at £500,000, Hibs, Aberdeen and Dundee United came in at £600,000. Rangers was very interesting, Graeme Souness was there, but they weren’t prepared to raise their offer," he recalled.
"When the chairman told me about the bids, it was Rangers out of the three that I wanted to speak to but the offer was too low. Wallace [Mercer, the Hearts chairman] eventually went that wee bit extra to get me back and the stars aligned.”
Robertson is full of praise for Hearts under Robbie Neilson and insists they have nothing to fear going to Ibrox.
“They have unity, you can see that. There’s a lot of improvement in this team because they have a lot of young lads. They can get better. They are playing with an arrogance but that’s controlled, not in your face. They know they are a decent side who, if they play well together, are as good as anybody in the league. Hearts have nothing to fear going to Ibrox.”