Having helped Rangers to win the Scottish title 10 times and the League Cup on nine occasions, very few have won more honours.
But there is an anomaly in the glittering CV of Alistair Murdoch McCoist.
Incredibly, he only lifted the Scottish Cup once in his long and trophy-laden career.
That happened back in 1992 when McCoist netted for the Gers in a 2-1 victory over Airdrieonians at Hampden.
David Robertson played alongside the legendary striker in that win - as well as in many other memorable triumphs in what was a halcyon era for Rangers.
And he admits he finds it unusual one of the country's most celebrated players only prevailed in the national cup competition once.
However, Robertson reckons that his old pal has a point to prove in this year's William Hill Scottish Cup as a manager due to that lack of success.
Speaking ahead of the fifth-round fixture between Rangers and Dunfermline at Ibrox tonight, he said: "Ally is, purely and simply, a winner.
"It is weird that he only won the Scottish Cup once as a player because right throughout his career Ally had this amazing habit of coming up smelling of roses.
"Look at all the goals he scored for Rangers. They came off every part of his body. Somehow the ball would always seem to go in the net.
"So it's strange that he only won the Scottish Cup once. I am sure he will be desperate to do well in the competition with Rangers now he is manager."
Robertson, now head coach with USL Pro League club Phoenix in the United States, has vivid memories of the Scottish Cup success over Airdrie in 1992.
But, strangely given it was his first victory in the competition since completing his £1million transfer from Aberdeen, they are not especially fond ones.
He revealed: "The one thing I remember clearly about that Scottish Cup final is that it felt like a defeat afterwards.
"Everybody expected us to beat Airdrie and beat them easily. Sure enough, we went 2-0 ahead through Mark Hateley and Ally.
"Andy Smith pulled one back for them, but we held on and just got over the finishing line. It wasn't the greatest game to play in or watch.
"It was a real anti-climax. We didn't have a normal celebration afterwards. It was probably the lowest I have ever felt after a victory.
"I can recall Archie Knox in the changing room afterwards. He told us: 'Cheer up! You've won the Scottish Cup! Nobody will remember you didn't play well!'
"We had enjoyed a great season. A few weeks earlier we had won the league. It was the first time I had won it and that was a fantastic feeling."
ROBERTSON added: "We completed the league and cup double with the win over Airdrie. But we were still down. It just shows you the standards that we had at Rangers at that time.
"I don't think we realised what we were achieving at the time. Winning trophies just became a habit."
Robertson, a classy left-back who is still, many years after leaving, highly regarded by Rangers fans, played a key role in the victory as well.
He helped put Walter Smith's side ahead against Alex MacDonald's team in the first half by setting up Hateley for the opening goal.
He said: "We scored quite early on. Nigel Spackman played a ball upfield to me, Davie Kirkwood slipped and fell, I controlled it and squared it to Mark Hateley.
"Mark was brilliant at getting in at the near post. He nipped in and netted. Hateley was one of the best forwards I have ever played with. He had a lot of pace and was so strong.
"Every time you put a ball into the penalty box you knew there was a good chance he would get to it. Even if it was a poor ball. He made you look good.
"He was good in the air and good on the ground. There are not many of those players around these days. But I don't think scoring early helped the game. We couldn't get into a rhythm. We just couldn't get going."
Robertson still keeps close tabs on how Rangers are faring and has been saddened with their recent plight.
However, he is glad that McCoist is the man who has been charged with the task of returning them to the forefront of the game here.
And he is hopeful that, with the experienced players he signed during the summer, they can beat Dunfermline and challenge the top-flight teams for the Scottish Cup.
Robertson said: "There is nobody I would rather have in control of Rangers just now than Ally with the issues they have had to deal with.
"Despite only winning the Scottish Cup once as a player, he knows what it takes to do it. I don't think you can write Rangers off this season."