#5 League titles
In his 8 complete seasons as a manager – the current campaign is his 9th – Pep Guardiola has only failed to win the league twice. Ever since he took over the reins of Barcelona's first team in 2008, he has won the league title an astonishing 6 times in the last 9 years.
If you leave out his yearlong sabbatical, then that is 6 titles in 8 years – a record that is far better than what Ancelotti could claim. Despite being one of the most decorated managers in the game, he has only three league titles in his 21 years of management.
For someone as reputed as the Italian, that’s a really poor return of league titles after being in management for so long. Ancelotti might have won three Champions League titles as a manager, but that is only one more than Guardiola, who has managed for 13 years less than the former Parma boss.