It is perhaps symbolic that, as he approaches his 500th match in charge at Manchester City on Sunday, Pep Guardiola is being confronted with so many problems that he hasn't faced since the very beginning of his tenure. He is completing a circle of sorts.
Guardiola's first City team in 2016-17 was a bit of a mess. Of the 22 players who saw at least 700 minutes in all competitions that season, 12 were at least 30 years old and five were 22 or younger. Midfielder Kevin De Bruyne, 25, was brilliant and nearing his prime while a pair of 28-year-olds, forward Sergio Agüero and defender Nicolás Otamendi, were stellar. But the squad itself had been allowed to grow stale before Guardiola's arrival, and expensive (and young) recent additions like Raheem Sterling, John Stones and Leroy Sané were still maturing, needing time to adjust to Guardiola's demands.
City enjoyed plenty of high points that season -- a nine-match winning streak to start the Guardiola era, a 3-1 thumping of Barcelona in the Champions League, an eight-match unbeaten streak to end the campaign -- but they finished 15 points behind Premier League champions Chelsea and bowed out to AS Monaco in the Champions League round of 16. Near the end of the season, Guardiola said that either of his previous clubs (Barcelona or Bayern Munich) would have fired him for his performance, and while that was almost certainly not true, it reflected the disappointment plenty felt.
Now, after 499 matches, City's current problems seem awfully familiar. Of the 19 players who have recorded at least 600 minutes in all competitions in 2024-25, 11 are 29 or older, four are 22 or under and only four -- forward Erling Haaland, midfielders Phil Foden and Matheus Nunes and defender Rúben Dias -- are close to what you might call the prime age range. (Foden, Nunes and Dias have all missed time with injury, too.) Injury and staleness have helped to derail a season that has seen some high notes and a 14-match unbeaten streak to start the season, and once again, Guardiola has spoken unrealistically of getting fired.
Guardiola and City approach match No. 500 in their worst ever form together, and with what is expected to be an active January transfer window approaching, the squad could soon feel almost as new as the 2016-17 iteration. But 500 matches is an incredible milestone all the same, and it's a really interesting moment to step back and take a look at Guardiola's first 499 matches -- and 354 wins -- in charge.
