Pep Guardiola and Mauricio Pochettino will meet in the Champions League semi-finals later this month, with the Argentine having faced no manager more often in his coaching career than the former Barcelona boss.
As players the pair represented city rivals Barcelona and Espanyol, with both going on to manage their respective clubs, so it's a rivalry that started on the field before continuing off of it.
Having locked horns in Spain and the Premier League, now they're gearing up for a mouthwatering clash in Europe's premier club competition. But how have they fared against one another so far in the dugout?
1. Espanyol vs Barcelona (21/1/2009)
The first leg of this Copa del Rey quarter-final turned out to be a 0-0 draw - not the most entertaining of matches to kick off what would go on to become an intense rivalry.
A much younger Lionel Messi was a substitute that day but having come on, even he was unable to break the deadlock.
2. Barcelona vs Espanyol (29/1/2009)
Barcelona won 3-2 in a highly entertaining second leg which saw Pep Guardiola's side progress through to the last four of the competition.
Bojan Krkic scored a brace before Gerard Pique added a third - putting the La Liga giants in a comfortable position. At least that's what they thought.
Pochettino's Espanyol showed great spirit, almost fighting back; Coro and Jose Callejon scored in the second half to close the deficit but it wasn't enough to avoid elimination.
3. Barcelona vs Espanyol (21/2/2009)
The teams would meet again just a month later, this time in league competition. Espanyol were to have their revenge at the Camp Nou when Ivan de la Pena netted a brace just after half-time.
Barcelona's Yaya Toure pulled one back for Guardiola's side but Pochettino had the last laugh that day, earning his first win over his rival.
4. Barcelona vs Espanyol (12/12/2009)
This particular fixture between the two was decided by a first-half spot kick.
Zlatan Ibrahimovic who has since described Guardiola as 'the most immature' coach he has ever worked with - make of that what you will - converted to earn his boss all three points.
5. Espanyol vs Barcelona (17/4/2010)
Once again, Pochettino's side were able to frustrate Guardiola's superstars by holding them to a goalless draw in the league at the business end of the season.
Dani Alves was sent off for a second yellow in the second period and that's about it as far as talking points from this one go.
6. Espanyol vs Barcelona (18/12/2010)
Finally, Guardiola's side registered a victory over Pochettino reflective of the gulf in quality between their two squads. In front of a packed RCDE Stadium, Barcelona thrashed Espanyol 5-1.
Pedro scored twice, David Villa also bagged a brace and Xavi got in on the act. It was a night to forget for Pochettino's men.
7. Barcelona vs Espanyol (8/5/2011)
Sitting pretty at the top of the league, Barcelona inflicted another defeat on their local rivals in the derby. This time it was a 2-0 win courtesy of goals from Andres Iniesta and Gerard Pique.
It was starting to feel like Pochettino would never taste victory over Pep Guardiola's mighty Barcelona again, at least not while he was in charge of Espanyol.
8. Espanyol vs Barcelona (8/1/2012)
Pochettino would go on to take one more point from Guardiola as Espanyol boss when his side scored a late equaliser through Alvaro Vazquez, after Cesc Fabregas had put Barca in front inside a quarter of an hour.
Vazquez's 85th minute goal sent the crowd of approximately 35,000 inside the RCDE Stadium into wild celebrations.
9. Barcelona vs Espanyol (5/5/2012)
The pair were to meet one more time as managers of these fierce rivals, but La Blaugrana made light work of Espanyol who were down in 13th place in La Liga at the time.
Pochettino discovered the talents of Messi first hand as he scored all four of Barcelona's goals.
10. Tottenham vs Manchester City (2/10/2016)
After more than four years of not having faced one another, Pochettino and Guardiola locked horns again, this time in the Premier League.
Although the former Barcelona boss enjoyed the superior record during their time in Spain, he won't have been pleased to see his old adversary get the better of him with a 2-0 win for Spurs.
Aleksandar Kolarov scored an own goal to set Pochettino's Lilywhites on their way, before Dele Alli added a second.
11. Manchester City vs Tottenham (21/1/2017)
Guardiola avoided successive defeats against the former Espanyol boss when they met later on in the season, but was denied three points despite his side having taken a two-goal lead.
Leroy Sane and Kevin De Bruyne put City into a commanding position but goals from Dele Alli and Son Heung-min salvaged a point for Pochettino's charges.
12. Manchester City vs Tottenham (16/12/2017)
It proved to be third time lucky for Guardiola against Pochettino in the Premier League. City ran out comfortable 4-1 winners thanks to goals from Ilkay Gundogan, De Bruyne and a Raheem Sterling double.
This was the first of the two meetings between the two sides in the 2017/18 season - a campaign in which the Cityzens went on to be crowned champions achieving a record points tally of 100.
13. Tottenham vs Man City (14/4/2018)
The second meeting between Guardiola and Pochettino in the league that season saw the Spaniard triumph over his old rival once again.
Gabriel Jesus, Ilkay Gundogan and Raheem Sterling scored in a 3-1 victory while Christian Eriksen netted Spurs' only goal of the game.
14. Tottenham vs Manchester City (29/10/2018)
Guardiola went on to register his third consecutive victory over Pochettino when the two sides met on matchday ten in the Premier League the following season.
This time, it was a narrow 1-0 victory at Wembley thanks to Riyad Mahrez's fourth goal of the 2018/19 campaign.
15. Tottenham vs Manchester City (9/4/2019)
Pochettino and Guardiola came face to face in the biggest clash between the pair to date, a UEFA Champions League quarter-final.
It was the perfect time for the Spurs boss to get one over his old rival and put a stop to his losing run. The Londoners won 1-0 thanks to Son's goal, and had a lead to take into the decisive second leg that was to follow eight days later.
16. Manchester City vs Tottenham (17/4/2019)
The highlight of Pochettino's career to date has to be the run he took Spurs on in the 2019 Champions League final, and to eliminating his old adversary en route must have been sweet.
It was a thrilling encounter with late drama. The second leg ended 4-3 in City's favour, but the Lilywhites progressed courtesy of the away goals rule.
17. Manchester City vs Tottenham (20/4/2019)
Three days later, the two managers met again, this time in the Premier League. Phil Foden scored the winner for Guardiola's men in a 1-0 win but even that wouldn't have remedied the heartache they suffered just days earlier.
Pochettino had been beaten by Guardiola again but with a Champions League semi-final on the horizon, he may not have been feeling so down in the dumps.
18. Manchester City vs Tottenham (17/8/2019)
The most recent meeting between the two bosses came in August 2019 and ended in a 2-2 draw. Sterling and Sergio Aguero were on target for Guardiola's men, while Erik Lamela and Lucas Moura contributed Spurs' goals.
Pochettino went on to be sacked just three months later and the pair have not met since. While the Spaniard holds the better record overall, losing to the former Espanyol boss in three of their 18 meetings - this time around Pochettino is equipped with a far stronger side.
19. Head-to-head record
Pep Guardiola: 10 wins
Mauricio Pochettino: 3 wins