Five men from Barcelona's class of 99 take on each other as Premier League managers

It was Barcelona’s centenary year, and after a disappointing elimination early in the Uefa Champions League, the supporters demanded something to show for the landmark. On the penultimate weekend of May 1999, they had it, the club’s 16th Spanish league title confirmed with three matches to spare. That day, away at Alaves, a Barcelona side with five Dutch players and three Spaniards in the starting XI went 3-0 up by the 68th minute. The trophy was assured. So manager Louis van Gaal took the precaution withdrawing his captain, to rest him a little. He brought on as substitute one of the players who, perhaps underused in the campaign, was deemed to be deserving of an active part in the celebrations. Watch Barca beat Alaves in 1999 It was Pep Guardiola who went off, and Mauricio Pellegrino, a tall Argentine defender, who came on to join a central defence marshalled by Frank de Boer. On the bench, at the final whistle Van Gaal embraced his assistant, a young Portuguese named Jose Mourinho. Another of Van Gaal’s deputies, Ronald Koeman, proudly added another Barca league title, this one as a coach, to the four he had won as a player at the club. Quite a collection of leaders and thinkers made up that Barcelona dressing room, then. No fewer than five of that group will be managing in England’s Premier League when it begins this weekend. That is 20 per cent of the league’s brain trust, as it were, all drawn from the staff of Barcelona 1998/99. De Boer, a summer appointment at Crystal Palace, and Pellegrino, the new manager at Southampton, prepare to take on the challenges of the most watched domestic football competition in the world for the first time. There is little doubt that having Barcelona on your resume carries a certain cachet in the modern game. It is not just that the Catalan club have been consistently successful – albeit with some lean phases - over the past 20 years, but that they have pointedly advertised their stylishness and their principles about how the game should be played. If Mourinho’s managerial career, about to go into its second season with Manchester United, has been defined by his achievement as a No 1 coach at clubs who rivalled Barca and characterised more by pragmatism that artistic flourishes, he certainly established a reputation as fine analyst while working on the Barcelona bench. Nobody, meanwhile, epitomises Barcelona’s pass-and-move panache more than Guardiola, identified as a fine midfield strategist by the great Johan Cruyff when Cruyff managed Barcelona in the late 1980s and early 1990s. Guardiola became a serially successful Barca manager before taking over the reins at Bayern Munich – and is now in charge of Manchester City. Cruyff inspired Koeman, now manager of Everton, and Cruyff’s ideas educated De Boer. The pair were adventurous defenders who regarded every clearance as an opportunity to launch an attack rather than a nervous emergency. They were appreciated at Barcelona for that quality. Pellegrino, who spent one season at Camp Nou – his chances restricted by the arrival of De Boer at the club – also combined physical authority with tidy distribution. As coaches, they respect elegance. Boer and Pellegrino presented to their new employers manifestos for entertaining football. It was a requirement. Southampton had dispensed with the services of Claude Puel, who managed them for a season and reached the League Cup final, partly because he was associated with a crabby, cautious approach. Les Reed, Southampton’s director of football, forecasts “high-intensity, attacking football” under Pellegrino, who guided low-budget Alaves into the top half of Primera Liga last season. Read Richard Jolly's preview package: De Boer, a candid talker with four Dutch titles as Ajax manager to his name, speaks of Palace’s evolution after having been steered clear of a tricky relegation threat with the functional methods of Sam Allardyce. “Great respect for Sam," De Boer said. "But if Palace signed me they know they are going to see something different.” Significantly, Palace had earlier explored the possibility of recruiting Pellegrino as Allardyce’s successor. The relative fortunes of these two newcomers to the Premier League touchline – 19 years after they duelled for a place in Barcelona’s defence – will be monitored closely. Both Palace and Southampton aspire to finishing in the top half of the table, and, beyond that, to the kind of position the impressive Koeman took Everton to last season: seventh. As for the other boys from Barca’s class of '99 – Mourinho and Guardiola – they target top spot. They know that anything less will be deemed a let-down. They also know how weighty a judgement will be made on which of them finishes higher in the Premier League than the other.

Five men from Barcelona's class of 99 take on each other as Premier League managers

Mourinho, Guardiola and Koeman have been joined by De Boer and Pellegrino, each tasked with taking their teams to new levels.