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Paris Saint-Germain and Manchester City, despite the serious injection of money into both clubs in recent years, have not been able to progress further than Leeds United in the Champions League.
That's right, it's not been a fun time for either the reigning Ligue 1 champions or current Premier League holders in Europe's top-tier club competition.
City were knocked out of the Champions League on Wednesday night after Tottenham Hotspur progressed through to the semi-finals thanks to the aggregate scoreline.
However, PSG suffered an earlier exit from the competition this season when Manchester United made a brilliant comeback in their second-leg clash last month.
Since the rebrand of Europe's premier club competition in 1992, neither PSG nor City have been able to outdo Leeds' best run in the tournament.
The Championship side featured twice in the tournament, with their first attempt ending in an exit in the second round after their defeat to Rangers in both legs.
However, Leeds made it into the competition in the 2000/01 campaign and beat 1860 Munich in the third round of qualifying matches, eventually reaching Valencia in the semi-finals before suffering a second-leg defeat.
Sure, City have featured in the Champions League for every year since they made their debut in the 2011/12 campaign, but it has very much been a hit-and-miss affair when it comes to progressing in Europe.
The furthest that City have come in the competition was in the 2015/16 season when they faced Real Madrid in the semi-finals. They secured a draw in the first leg, only to lose 1-0 in the second leg to Los Blancos.
Prior to the Qatar Sports Investments' purchase of PSG in 2011, the French side made their best stint in the Champions League when they reached the semi-finals in the 1994/95 campaign against AC Milan.
With the QSI backing, however, PSG's furthest progress in the Champions League has been the quarter-finals on four occasions.
Of course, the Ligue 1 side hold the two biggest transfers in football history, having signed Neymar from Barcelona for a world-record fee of €222m and Kylian Mbappé from Monaco for €180m.
Which teams will make it to the Champions League final this season?
Let us know in the comments.
Featured Image Credit: PA
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