In a distinguished managerial career spanning 18 years, Pep Guardiola is poised to reach a significant milestone this weekend as he takes charge of his 1,000th game as a head coach. His illustrious journey includes stints with Barcelona, Bayern Munich, and currently, Manchester City. It is particularly fitting that this landmark match occurs against Liverpool, a club that has consistently posed the greatest challenge to Guardiola during his successful tenure at City. Currently in his tenth season at the Etihad Stadium, Guardiola has secured six Premier League titles, notably overcoming Jürgen Klopp’s Liverpool in both the 2018-19 and 2021-22 seasons. In the two seasons where Guardiola did not clinch the league title, 2019-20 and 2024-25, Liverpool triumphed, first under Klopp and then under current manager Arne Slot last season. While Guardiola has had notable rivalries, particularly with José Mourinho during their times at Barcelona and Real Madrid, he acknowledges that Klopp has been his most formidable adversary. As he prepares for Sunday’s historic fixture, Guardiola expressed, “If I were to choose one rival for this personal milestone that I want to share with many people, they [Klopp’s Liverpool] would be the best.” Guardiola reflected on his time in England, emphasizing the lasting impact of his experiences with Barcelona and Bayern Munich, but noted that Liverpool, especially under Klopp, has provided him with the most significant rivalry in the Premier League. He stated, “It could not be better, to be honest. So destiny decided that, and it’s nice to live it.” The influence of Klopp on Guardiola is profound, as the two have faced each other during previous tenures at Borussia Dortmund and Bayern Munich. Guardiola admitted, “I miss him. He gave me a lot in terms of challenging me to think, work, and improve in order to defeat him.” Reflecting on his remarkable longevity as a manager, especially given the pressures associated with leading three elite clubs, Guardiola acknowledged the inherent difficulties of life on the sidelines. He remarked, “The numbers are insane. I’m not living thinking of how many, but when you have the milestone and you read what you have accomplished—the victories and averages across competitions—it’s clear how difficult it is to achieve this.” As City gears up for the match against Slot’s Liverpool, they aim to make it a perfect day for their manager, entering the contest in strong form with only one loss in their last 13 games across all competitions. Meanwhile, Liverpool is experiencing a resurgence after a challenging period, having recently won their last two matches, including a 2-0 victory over Aston Villa, thanks to goals from Mohamed Salah and Ryan Gravenberch. Post navigation Guardiola Set to Reach 1,000th Match Milestone Against Liverpool Trinity Rodman’s Status Uncertain Ahead of NWSL Quarterfinal