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

Kane Bayern United GFX

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.

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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 Kane.

The England captain was United's No.1 target towards the end of last season as he approached the final year of his contract with Tottenham. They had their reasons for not going through with it in the end, though, and have instead taken a punt on their long-term future by signing Rasmus Hojlund instead, as well as strengthening their squad in other areas.

But after making a woeful start to the season, losing three of their first five Premier League games for the first time ever as well as being afflicted by a never-ending list of off-field problems, the fact United missed out on Kane should give the club a pause for thought. A decade ago they would have done whatever it took to sign one of the best players in the world. Had Ferguson still been in charge and different owners at the helm, they would have pulled out all of the stops to sign Kane. They would have done what Bayern did.

They fact they did not, and that Kane did not push for a move to Old Trafford, shows how far they have fallen in comparison to the Bavarians. Not long ago United considered Bayern their equals, but now they are in almost a different league...