When Neilson won his only international cap, coming on in the final minute of a 2-0 defeat to Ukraine in Kiev in 2006, McCulloch had earlier withdrawn from the squad due to injury.
They were, for the most part, rivals. That was certainly the case in the 2014-15 season when Neilson, having landed the manager’s post at Hearts, proceeded to prove just what an astute appointment he had been by leading the Tynecastle side to the Championship title at the expense of McCulloch’s Rangers, among others.
Now firmly on as well as by Neilson’s side as his assistant ahead of this afternoon’s Scottish Cup final against Celtic, McCulloch began to gravitate towards his future boss during that campaign.
“I was speaking to him a lot because I was intrigued with what he was doing in training,” he recalls. “I was impressed, but I was just trying to learn as a coach at the time and get as information out of him as possible. Now we’ve come together, along with Gordon Forrest, who is a tremendous coach…”
Neilson moved on after that initial Hearts spell as manager. Likewise McCulloch, who briefly managed in his own right at Kilmarnock and then found himself out of work after another short spell coaching in Poland. To widespread surprise, Neilson brought him in as strikers’ coach at Dundee United in what seemed an initially loose arrangement. He was appointed assistant head coach in June last year and helped Neilson steer United to promotion in a Covid-19 affected season.
No sooner had the celebrating United manager’s lips left the rim of a Corona bottle, he was off back to Hearts. This decision underlined Neilson’s ruthless streak. It also left the immediate future uncertain for McCulloch and Forrest.
It was clear Neilson wanted his staff with him and McCulloch helped force the issue, when he was described as “walking out” of his Tannadice post shortly after Micky Mellon’s arrival. He and Forrest were confirmed as joining Hearts in August.
It was another example of the quietly spoken Neilson getting what he wanted. McCulloch has observed Neilson at close quarters over the course of a couple of years now and sees shades of someone as celebrated as Walter Smith, his former manager at Rangers and Scotland.
That’s not to say Neilson’s taken to sporting a sleeveless cardigan. He elected to wear a rather bold blue tweed check suit when being unveiled by Hearts for a second time in July. And, indeed, McCulloch sees Neilson as a blend of modern and old, someone who, while approachable, doesn’t, as with Smith, suffer fools gladly.
“He’s very mature, he reminds me - and I'm not trying to put pressure on him - of Walter Smith,” says McCulloch.
“He has the serious look, he has the nasty side, a touch of old school mentality. But I feel he’s a modern day coach with his set-up. The way we go through the opposition, there’s a lot of video analysis done and he’s only going to get better as well.
“When you look at being in Europe with Hearts the first time, winning the league with Dundee United and then coming back to Hearts, he’s had experiences, including his spell in England with MK Dons, even if that didn't go the way he planned it to. But sometimes when you don’t do so well you learn more than you do winning all the time.
“So, he’s been tested,” he adds. “I believe he’s in the top five managers in Scotland, without a shadow of a doubt. I’m not saying he’s won enough stuff to back that up but I can only go on what I’ve seen and he’s 100 per cent in the top five by a mile.”
That’s quite an accolade for someone who has, in recent times, been operating in the second tier. McCulloch clearly think he belongs in the company of men like Steven Gerrard and Neil Lennon, who he is attempting to outwit today, as well as Derek McInnes and Jack Ross, the other managers one must supposes make up the list of the proposed top five.
Neilson will further enhance these credentials should he lead Hearts to glory this afternoon, thereby adding to the two Championship titles won at Tynecastle and, most recently, at Tannadice.
As a two-times Scottish Cup winner with Rangers, McCulloch will be especially helpful, although on both those occasions he was in a team expected to win against Falkirk and Queen of the South, who, like Hearts this afternoon, were from the division below. Curiously, when Neilson earned his sole Scottish Cup winners’ medal as a player, it was in 2006 against Gretna, then from two divisions below Premier League side Hearts.
Both Queen of the South and Gretna gave their more illustrious opponents something to think about, which will give McCulloch and Neilson encouragement. Hearts, of course, will contend they are a top-flight club in all but current status, having been relegated in such controversial fashion.
Nevertheless, Celtic, whatever their current problems, deserve respect. Hearts, however unsatisfactory were the circumstances leading to them being deposited in the Championship, are profound underdogs against a side who have won 11 straight domestic honours.
McCulloch has watched Celtic often recently and can see they are creating as many chances as ever. “I think their manager will come out and tell you that, he's someone I have massive respect for,” he says with reference to Lennon.
“We are certainly not buying into the thinking players who have contributed to winning the last nine championships in a row all of a sudden cannot play football any longer. We are certainly not buying that.”
Lee McCulloch was speaking at a William Hill media event. William Hill is the proud sponsor of the Scottish Cup