The 41-year-old is no stranger to some of the most fiercely contested rivalries in British football, both as a player and as a manager.
He can reel off a plethora of all-Yorkshire tussles from his stints with Bradford, Barnsley and Wednesday, while he was involved in the always fiery East Anglian showdown against Ipswich Town while on the books of Norwich City.
Since hanging up his boots, Heckingbottom has managed Barnsley to a victory against Leeds and, having crossed that divide in February 2018, then guided Leeds to a victory over Barnsley. He is a man who does not require a crash course on what derby day means to a city.
Nevertheless, it is that outing for Wednesday in February 2005 that sticks in Heckingbottom’s mind. Recalling the abuse he received from his Barnsley-daft friends and family, the rancorous atmosphere at Oakwell and the swathe of wild challenges, he is visibly wistful.
Let the record show – in typical derby fashion – an attritional contest finished 0-0 as the Owls, who also included Hearts striker Steven MacLean, escaped with a point.
“The tastiest derby I played in would have been for Sheffield Wednesday at Barnsley,” Heckingbottom smiled. “When you even have your own friends and family wanting you to get beat and get hurt… that was a strange one.
“Most Barnsley people would say Sheffield Wednesday is the big derby. They were bigger games and were the ones that fans got really up for, as they were the closest team. It had everything – the fans, the atmosphere. It was the one that got the juices flowing.
“I actually got sent a video of that game. It was just a little clip, probably around 30 seconds, and there were about five tackles. I was involved in three – and four of them should’ve been red cards! The game just carried on.
“They would have been red cards now. It gets the fans and the crowd fired up; the cheers, the roars. That’s what’s changed down in England. The build-up is the same as it always was but the actual product on the pitch and what it looks like is totally different to what it was.”
The tone of regret is unmistakable.
Heckingbottom is every inch the modern coach in terms of his implementation of analytics, GPS and focused video presentation, but there is something of the old school defender in his assessment of how the ferocity of derbies has been watered down south of the border.
It is one of the reasons he cannot wait to experience the blood and thunder of an Edinburgh showpiece, officiated with what he perceives as additional leeway afforded by SPFL referees.
“You need to change with the times but I would complain down south when you could see fouls coming,” he continued.
“You’d see that the player was going to put on the brakes, step across an opponent who’s at the back of him and win a free-kick.
“So how is it a free-kick? None of that up here. That would be ‘get up’ and I like that side of it.
“It’s probably changed a little bit up here as well – but there’s still contact here, it’s more physical with more tackles and the atmosphere reflects that.”
Heckingbottom pointedly notes that he used to relish being the away side come derby day, with the prospect of upsetting the odds and silencing the masses a tantalising one.
He is hopeful that attitude will be mirrored by his players as they make the journey to face Hearts tomorrow lunchtime in what he believes will the most stringent test of their mettle since he took the reins.
“This will be Hibs’ biggest test so far – and will be a different type of test,” added Heckingbottom. “The challenge is still to get three points but it is a derby and there is a rivalry there and it is all about handling the intensity of the occasion.
“Tynecastle is a different stage and a different environment to play in. It will be good to see how my players respond to that.”
Heckingbottom was speaking after collecting the Premiership manager of the month for March following an impressive start to his tenure at Easter Road.
However, he has no fear that the award may prove to be the infamous kiss of death. He smiled: “I knew before the Kilmarnock game that I had won it – and we did OK there.”
l Hearts and Hibs have urged their supporters to “Respect the Rivalry” in tomorrow’s Edinburgh derby through a joint video campaign under the tagline “Two clubs. One city.”
The capital clubs both posted videos on Twitter featuring a selection of players talking about the derby matches they have taken part in.
Among them were Liverpool v Everton, Barnsley v Sheffield Wednesday, Dundee v Dundee United, Fenerbahce v Galatasaray, Celtic v Rangers, Genoa v Sampdoria and Norwich v Ipswich. A selection of players use words to describe the matches – “electric, intense, hectic, fiery” – before urging the fans to “keep the action on the pitch”.
The clips are a plea from both clubs for supporters to be on their best behaviour during tomorrow’s showdown in the wake of several unsavoury incidents at high-profile Scottish games.