Eighteen years after they first met, Leicester boss Brendan Rodgers and Roma's Jose Mourinho will do battle on Thursday for a place in the Europa Conference final.
It may not be a competition that either had high up on their career ambitions - in fact Rodgers wasn't even sure what it was when the Foxes were dumped into it via being knocked out of the Europa League - but with the score locked at 1-1 the second-leg tie in Italy has significance for both coaches.
Mourinho and Rodgers worked together during 'the special one's' first spell in charge at Chelsea. Rodgers was a youth coach with the Blues after being brought in from Reading's academy in 2004, before going on to manage Swansea City, Liverpool and Celtic, among other teams.
He has long since confirmed his status as one of the foremost domestic coaches of his generation, so attempting to bill the tie in Italy as the apprentice trying to upstage the master would be a stretch too far.
However, the encounter at the Stadio Olimpico does have the potential to underline Rodgers' passing of Mourinho in the current coaching hierarchy.
Not, obviously, in terms of career achievement. With eight league titles across four countries and two Champions League triumphs the highlights of a silverware-laden career, Mourinho is well established as one of the greatest coaches of the modern era.
But Mourinho's last significant triumph was also Manchester United's, when they won the Europa League in 2017. So, for 59-year-old Mourinho, the Leicester game matters.
For Rodgers, 10 years the Portuguese's junior to the day, guiding Leicester into a first European final would confirm him as a man of the future, while further highlighting the notion of Mourinho as a man whose time has passed.
|Jose Mourinho's managerial honours|
|Porto (2002-04)||Primeira Liga (x2), Champions League, Uefa Cup (now Europa League), Portuguese Cup|
|Chelsea (2004-07 and 2013-15)||Premier League (x3), FA Cup, League Cup (x3)|
|Inter Milan (2008-10)||Serie A (x2), Champions League, Coppa Italia|
|Real Madrid (2010-13)||La Liga, Copa del Rey|
|Manchester United (2016-18)||Europa League, League Cup|
Not that Rodgers would say so. He has too much admiration for the man who helped shape his career.
"A special man," is how Rodgers described Mourinho before last week's first leg.
Mourinho's football philosophy has centred around power and strength. Rodgers' is more intricate and stylish yet they share the same attention to detail. They both have the same hunger to get every facet of the game-plan right.
"He was detail orientated," said Rodgers of Mourinho. "His man-management with players. His understanding of the tactical adaptations of the game and how you could promote that with the players.
"He had this special quality. It was interesting in my formative years as a coach to see how he could bring people along with him."
Rodgers was intrigued by Mourinho's charismatic approach to the job, at least from a media perspective, sometimes even standing at the back of the room at press conferences to get an understanding of the unique way he dealt with the assembled journalists.
"I haven't forgotten what I gained from him as a young coach," said Rodgers. "I studied him and watched him. I was in pole position for that."
Yet, when he was asked to join the first-team department at Chelsea, Rodgers declined, preferring to remain reserve team boss as that role allowed him to spend more time on the grass, as it is termed now, actually coaching, which he regards as his strength.
This should not be interpreted as a snub. Nor should there be any sense of Rodgers lacking respect for Mourinho's methods.
Criticism of Mourinho, Rodgers has previously argued, comes from those who have no idea what it is like to be on the touchline, feeling the intense pressure of trying to deliver results, game after game, week after week.
"I was at Chelsea for four and a bit years. He was there for three of them," said Rodgers. "The teams I saw him coach, he coached them to be aggressive. There is nothing wrong with that. He sets up his teams to make them very difficult to beat. That is OK too.
"He is one of the greats of our generation. He has nothing to prove to anyone. He is a winner. He will always be a winner."
That, clearly, does not stop Rodgers from having a fierce desire to beat Mourinho.
He wants the Portuguese wine he gave the former Real Madrid, Inter Milan, Manchester United and Tottenham boss before the first leg not to be accompanied by the bitter taste of defeat when they share a drink post match.
Speaking to the Football Association's 'Boot Room' a decade ago, Rodgers underlined a managerial philosophy that came from his own, limited, playing career, when he realised he was spending more time without the ball than with.
"The culture was very much long and direct and that didn't suit me as a player," he said.
"I was a technician but the games I was asked to play in were not how I enjoyed playing. I started on a journey to try and make young players feel important and give them confidence to deal with the football."
So, the playing out from the back, the short goal-kicks to defenders inside the penalty area, goalkeepers comfortable in possession, the methods Pep Guardiola and Jurgen Klopp are using to march Manchester City and Liverpool to the top of the European game, come very much out of the Rodgers playbook.
In contrast, Mourinho is seen as a bit of a dinosaur, increasingly drawn to being secure at the back and trying to hit on the counter. With 68% possession and 13 shots to four in Leicester's favour, that is how bare statistics tell the story of last week's first leg.
This is unfair on Mourinho though and Leicester should prepare to meet a more expansive Roma in the Italian capital.
An intriguing contest can be anticipated.
For the victorious manager, there will be the chance to contest the inaugural Europa Conference League in Tirana on 25 May - perhaps accompanied by slight bragging rights over their former colleague.