How many times has Pep Guardiola won the Champions League? Pep Guardiola won three titles in 2009, 2011, and 2023, with Barcelona and Manchester City. Brian Clough won back-to-back titles as manager of Nottingham Forest. Ernst Happel was the first manager to win the title with two different clubs. Ottmar Hitzfeld, winning manager in 1997 and 2001. He won both of the first two titles as manager of Barcelona in the 2008/09 and 2010/11 seasons. The Spanish side reached the final of the 2009 edition of the competition, beating Bayern Munich and Chelsea on their way. Guardiola won two Champions Leagues with BarcelonaCredit: Getty Guardiola’s next Champions League came two years later in 2011 when Barcelona beat Man United once again in the final They faced Sir Alex Ferguson’s Manchester United in Rome and won 2-0 thanks to goals from Samuel Eto’o and Lionel Messi. Guardiola lifted his first Champions League while leading his side to become the first Spanish team ever to win the treble.