Bayern Munich and Man Utd are now miles apart - only the Bundesliga side can challenge for the Champions League after going all out for Harry Kane

The Bavarians are one of the favourites to win the competition after landing the England captain while the Red Devils are a mess on and off the pitch

Bayern Munich versus Manchester United was once a classic Champions League fixture. The two giants had never met in the European Cup era, but then played each other 11 times in the space of 16 years.

The most famous meeting is, of course, the 1999 Champions League final at Camp Nou when United turned a 1-0 defeat into a 2-1 win in the space of three minutes. But the 2009-10 quarter-final tie was also epic, with Bayern coming from behind in both legs to eventually go through through on away goals. The Bavarians also prevailed in the quarter-finals in 2000-01 and at the same stage in 2013-14, when David Moyes' United briefly led against Pep Guardiola's Bayern before a quick-fire turnaround.

However, Wednesday's match at the Allianz Arena is the first meeting between these European juggernauts in nine years. And the reason for the long gap is not down to chance. Bayern have reached the Champions League quarter-finals in each of the last 10 years, including four semi-finals and one final (which they won). United, however, have only reached the last eight once since then, and have failed to even qualify for the competition on four occasions. While the Red Devils last won a Premier League title in 2013, Sir Alex Ferguson's final year in charge, Bayern have won the last 11 Bundesliga crowns.

The two clubs' contrasting fortunes are no coincidence. While United have been run in a shambolic manner since Ferguson retired, Bayern are arguably the best run club in Europe. And it was thanks to their management that they were able to beat United to the biggest signing of the summer: Harry