Brendan Rodgers and Jose Mourinho first met 18 years ago, and they will meet again 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.
The special one and the first one to be in charge at the club worked together. After working as a youth coach with the Blues, Rodgers went on to manage a number of teams, including Celtic.
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.
The match at the Stadio Olimpico has the potential to show Rodgers' passing of Mourinho in the current coaching hierarchy.
Not in terms of career achievement. One of the greatest coaches of the modern era is Jose Mourinho, who has won eight league titles in four countries and two European Championships.
Manchester United won the Europa League in 2017, their last significant triumph. The game is important for the 59-year-old.
For Rodgers, 10 years the Portuguese's junior to the day, guidingLeicester 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.
Club | Major trophies |
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 |
Tottenham (2019-21) | None |
Roma (2021-22) | None |
Rodgers wouldn't say so. He admires the man who helped shape his career.
Before last week's first leg, Rodgers described the man as a special man.
Power and strength have been the focus of the football philosophy of the man. Rodgers is more stylish and intricate than they are. They both want to get every facet of the game-plan right.
Rodgers said that he was detail oriented. His understanding of the tactical changes of the game could be promoted with the players.
He had a special quality. In my formative years as a coach, it was interesting to see how he could bring people along with him.
Rodgers was intrigued by the 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 studied him and watched him, and I have not forgotten what I gained from him as a young coach. I was in a good position for that.
When he was asked to join the first-team department, Rodgers declined, preferring to remain reserve team boss, as that role allowed him to spend more time on the grass, which he considers his strength.
This shouldn't be seen as a snub. There should be no sense of Rodgers not respecting the methods of the man.
Rodgers has argued that the criticism of Mourinho comes from people who don't know what it's like to be on the touchline.
For four and a bit years, I was at Chelsea. Rodgers said that he was there for three of them. There is nothing wrong with that. He makes his teams very difficult to beat. That is okay as well.
He is one of the greats of our generation. He doesn't have anything to prove to anyone. He is a winner. He will always be a winner.
That doesn't stop Rodgers from wanting to beat him.
He wants the Portuguese wine he gave the former Real Madrid, Inter Milan, Manchester United and Spurs boss before the first leg not to be accompanied by the bitter taste of defeat when they share a drink after the match.
A decade ago, Rodgers spoke about a managerial philosophy that came from his own limited playing career, when he realized he was spending more time without the ball than with.
He said that the culture was long and direct and that didn't suit him as a player.
I was a technician but the games I was asked to play 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.
The way in which Manchester City and Liverpool are playing, the way in which the goalkeepers are comfortable in possession, and the way in which the playing out from the back come from Rodgers's methods.
In contrast, Mourinho is seen as a bit of a dinosaur, drawn to being secure at the back and trying to hit on the counter. The bare statistics tell the story of last week's first leg, with the majority of possession and 13 shots to four in the favour of the home team.
This is unfair on the man and he should be prepared to face a more expansive Roma in the Italian capital.
An intriguing contest can happen.
There will be a chance for the victorious manager to face their former colleague in the inaugural Europa Conference League in Tirana on 25 May.