Ross cites his first visit to Parkhead, at the helm of Alloa Athletic as a defining moment in his coaching career.
Having left his role as Hearts’ under-20s manager, Ross was quietly cultivating a fine reputation in charge of Alloa in League One, implementing an attractive brand of football as they sought to bounce back from relegation and return to the second tier.
However, he acknowledges that he needed a breakout moment; a fixture to make Scottish football at large take notice of his Wasps side. That came in the quarter-final of the League Cup on 21 September, 2016.
Well-drilled and diligent, part-time Alloa held firm for 83 minutes against Celtic before finally succumbing to a 2-0 defeat. The favourites progressed but Ross and Alloa received ample credit.
“When you go into coaching or management you probably need certain moments to happen for you and things to fall your way,” recalled Ross.
“Alloa had a good cup run, drew Celtic and performed well on the night. Those little bits of fate go your way and help you get some attention as a manager, providing the team does okay.”
And as Celtic marched on, so too did Ross.
He was appointed manager of St Mirren two months later and immediately cemented his reputation as one of Scotland’s brightest young coaches, saving the Buddies from relegation before winning the Championship title in 2017-18.
In the midst of that journey, he returned to Celtic Park with the Paisley outfit, exiting the Scottish Cup in March 2017 with a 4-1 defeat. However, St Mirren did take the lead through Harry Davis before four goals in 20 second-half minutes turned the tide.
Former Celtic manager Brendan Rodgers – then in the midst of his all-conquering first season at the club during which they never lost a domestic match – famously stated that St Mirren had been Celtic’s toughest opponents of the campaign to date.
“Moments like that help build you as a manager,” said Ross. “We lost both games but we had good moments in both games as well.
“It gave me confidence that I was on the right path. Some people go into management with all these set ideas of things they’re going to do.
“I had an idea of what I wanted to in terms of managing people but, from a coaching point of view, I was more flexible and willing to adapt to find the best way to try to win games.
“Those two matches did give me an injection of confidence regarding how you see the game and what you want to get from it.
“It can be a brutal industry, people are constantly questioning what you’re doing and whether you’re good enough to do it. So when you get those little lifts along the way it does help.”
That respect Ross earned from Rodgers, now doing a marvellous job at Leicester, proved durable. The duo spent time together at Celtic’s Lennoxtown training base and, rather packed diaries notwithstanding, are always ready to meet for a chat.
“He was really good with me after the Alloa game and said that if there was anything I needed just to let him know,” continues Ross. “Then on the back of the St Mirren game I went to Lennoxtown a couple of times.
“It was good for me early on to have a recommendation from someone like him – and it was nice to be able to go toe-to-toe with his team over those two games. You’re coming up against managers who you know are good at what they do, so it’s always good to be able to test yourself.
“We played against a couple of Premier League teams when I was at Sunderland and that was the same – Chris Wilder and Sean Dyche are both really good managers and I enjoyed it. I don’t find it intimidating. I enjoy the challenge.”
Today’s fixture provides a different dynamic to Ross’s previous endeavours at Celtic Park.
Alloa and St Mirren were written off before a ball was kicked. However, Hibs, while underdogs, arrive in Glasgow on a run of four wins and a draw from their last six fixtures and thriving amid their new manager bounce.
Ross is also a far more experienced, well-rounded coach following a challenging 17 months in charge of one of England’s fallen giants, Sunderland.
“I’ve gained a lot of experience over the last year-and-a-half in big matches and in big stadiums,” adds Ross. “This feels a bit more normal for me now.
“Going to Celtic Park for the first time with Alloa was a really big deal but once you’ve done it once it just feels like work after that.
“You’re just doing your job – and I know what my job is on Sunday.”