MN: Milan and Chelsea meet again – the previous meetings and mercato history

By Oliver Fisher -

AC Milan were drawn in the same Champions League group as Chelsea for the first time in over 20 years as two clubs who are nonetheless very familiar with each other will fact off.

As MilanNews recall, the only previous UEFA competition meetings between the two teams dates back to 1999-00 when Silvio Berlusconi’s side met Chelsea who had not been taken over by Roman Abramovich yet but were enjoying the magic of Gianfranco Zola.

A 0-0 in London in the opening match of the group stage was followed up by a 1-1 at San Siro in a crucial match that Milan could have done with winning, given they crashed out in the next and final group match against Galatasaray.

There is also a mercato sub-plot to the Rossoneri meeting the Blues, starting with Andriy Shevchenko who moved to the London club for €45m in 2006. Dalla Bona arrived at Milan as a promising youngster and although he struggled, he ended up with a Champions League winner’s medal.

Hernan Crespo came on loan for a season from Stamford Bridge and in the Champions League he did well, and he would have hero of Istanbul had it not been for Liverpool’s comeback. Fernando Torres didn’t do as well, while neither did Marco Van Ginkel. Marcel Desailly and George Weah are two other big names to play for both.

Then there is the current crop. Tiemoue Bakayoko’s time at Milan can be split into two halves with a successful loan in 2018-19 followed up by a not as positive return. For Fikayo Tomori and Oliver Giroud, only positive things can be said.

Finally, the future. Rafael Leao has been linked with a potential move to Chelsea but it seems it would take an amount close to his €150m release clause – one not valid in the last two weeks of the window – to even tempt Milan.

Tags AC Milan


    1. Don’t remind us about him! One of the worst Milan signings this century. He didn’t even play a single good minute in the Rossoneri.

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