Two of the greatest managers of all-time, who have managed some of the greatest players of all-time.

Jose Mourinho is a Premier League champion x3, La Liga winner, Serie A winner x2, Portuguese Liga winner x2, Champions League winner x2, UEFA Cup/Europa League winner x2 and a total of 8 domestic cups – making him one of the most successful managers ever. He is still, to this day, the only manager to have won Serie A, La Liga and the Premier League. Those four European trophies have also come with three different clubs.

Pep Guardiola is looked upon as a true pioneer in the management game, with his possession based style has won the Premier League x2, Bundesliga x3, La Liga x3, Champions League x2 and a grand total of 8 domestic cups in his 12 years a senior manager. His style of football has influenced multiple managers to attempt similar things, with keeping the ball on the ground and a goalkeeper who can use his feet as well as his hands now a staple at most top clubs in the world.

The two managers have had a heated rivalry throughout their careers, starting with when Mourinho knocked Pep’s Barcelona out of the Champions League with Inter Milan with his trademark ‘park the bus’ style. It continued when he moved to the Spanish capital and managed Real Madrid, fierce rivals to Pep’s Barcelona. The Catalan had the advantage there though, as despite them sharing a league title each Guardiola also won the Champions League, knocking Mourinho’s side out in the semi-finals.

But what if you put together the best XI’s they’d ever managed and put them against each other? Firstly, you’ve got to pick the teams.

By default, Pep’s side will be mainly dominated by his Barcelona days. Arguably the greatest club side ever, Dani Alves, Gerard Pique, Xavi, Andres Iniesta, Sergio Busquets and Lionel Messi are absolute certainties. Eric Abidal, Victor Valdes and Samuel Eto’o all have a shout too from that side, but I’m leaving them out. At Bayern, Manuel Neuer and Philip Lahm walk into the side also while Arjen Robben gives himself a massive chance of getting into the team. At Man City, Aymeric Laporte is the only one assured of a spot. Raheem Sterling has been splendid as have Sergio Aguero, Kevin De Bruyne and David Silva but they all face still competition.

For Mourinho, it’s a harder task. So many players and titles but usually with different styles at different clubs. In goal, Petr Cech during his first spell at Chelsea is a shoe-in. In defence, John Terry and Ricardo Carvalho’s partnership at Chelsea makes it hard to break them up while Frank Lampard and Didier Drogba are also starters. Legends like Angel Di Maria, Samuel Eto’o, Wesley Sneijder and Zlatan Ibrahimovic all have big claims to be in the side but all miss out in the end as Cristiano Ronaldo and Eden Hazard take the wide positions.

Stylistically, Mourinho’s side is incredibly flexible. They have the ability to play possession football and pick teams apart while they could also be a sturdy defensive unit and play on the counter-attack. They’d without a doubt be a threat on set-pieces too with Drogba, Ronaldo and John Terry in the same team.

Pep’s side stays true to his style and has huge ability in playing his favoured style. The side will 100% play to keep the ball and when they lose it will press high. Two inverted wingers will allow both full-backs to overlap and provide extra width in attack, leaving more space for the midfield geniuses to create.

The big difference between the two sides though, is Lionel Messi. While Mourinho has Cristiano Ronaldo during the absolute peak of his powers, Guardiola has the little Argentine. Messi’s unbelievable ability to create 30+ goals a season in all competitions as well as score 60+ separates him from Ronaldo in the conversation about who is the greatest ever and with Messi in his favoured False 9 role here that could prove the big difference.

With Mourinho’s record in big games, there likely wouldn’t be a lot of goals and with Pep’s style of keeping the ball for 70% of the time it’s just obvious that they would be more likely to score. While you can’t rule out Jose’s side with the absolute mountain of ability they have, Pep’s boys will take home the W in my eyes with a 2-1 win courtesy of Lionel Messi magic.