Pep Guardiola has officially surpassed Sir Alex Ferguson to claim second place for the most games managed in Champions League history. However, this historic milestone was heavily overshadowed by a bitter reality, as his Manchester City side crashed out of the competition following a 5-1 aggregate defeat to Spanish giants Real Madrid in the round of 16.City’s Champions League journey ended in absolute disaster following a 5-1 aggregate thrashing by Real Madrid. After a crushing 3-0 first-leg defeat where Federico Valverde scored a spectacular hat-trick, the second leg quickly turned into a nightmare. Bernardo Silva was sent off for blocking a Vinicius Junior shot with his arm, conceding a 22nd-minute penalty that the Brazilian converted to kill off any remaining hope. Erling Haaland pulled one back with a 41st-minute strike, but Vinicius destroyed them with a late stoppage-time goal to seal a 2-1 win. Madrid will now face either Bayern Munich or Atalanta in the quarter-finals. The German side hold a commanding 6-1 lead from their first leg, making them the overwhelming favourites to progress.Despite the devastating exit, the second leg marked a monumental personal achievement for the Catalan manager. It was his 191st match in the dugout in Europe's premier competition, officially taking him past legendary Manchester United boss Sir Alex Ferguson.He had equalled the iconic Scotsman’s tally of 190 games during the disastrous first leg in Spain. His remarkable longevity in the tournament reflects his sustained excellence across highly successful spells with Barcelona, Bayern Munich and his current club, where he has consistently reached the latter stages of the competition over the past decade.While the 55-year-old has now distanced himself from the likes of Arsene Wenger, who managed 178 games, and Jose Mourinho on 154, he still has a significant gap to bridge at the top. The outright record-holder remains Carlo Ancelotti, who has managed an incredible 218 matches. Guardiola’s legacy is built on his impressive trophy haul, having won the tournament three times. These three titles place him joint-second on the all-time list alongside Bob Paisley and Zinedine Zidane, though he still trails Ancelotti, who currently boasts five historic victories.Add GOAL.com as a preferred source on Google to see more of our reportingThe European elimination continues a miserable March curse for the Manchester club. Aside from an FA Cup victory over Newcastle, City have stumbled domestically, drawing with Nottingham Forest and West Ham. This poor run has allowed Arsenal to take control of the Premier League title race, building a commanding nine-point lead at the top of the table, although the Gunners have played 31 matches compared to City's 30. Guardiola's men must quickly refocus to salvage their season, starting with a crucial Carabao Cup final against Arsenal this Sunday, before facing Liverpool in the FA Cup quarter-finals in April.