Pep Guardiola's quest to bring the Champions League title to Manchester City drags on.

While there is no denying that the legendary coach has been a success at the Etihad Stadium, his tenure risks being defined by failing to secure the trophy that the Citizens so badly desire.

Since the Spaniard took over in the summer of 2016, City have crashed out in the round of 16 once, exited the quarter-finals on three occasions and lost this year's final to Chelsea.

Man City's European woes

And one of the biggest criticisms lodged at Guardiola's shortcomings in Europe has been the fact that Sheikh Mansour has backed the endeavour with transfer spending of historic proportions.

In fact, according to Transfermarkt, City have the biggest net spend of any football club in the world since Guardiola's appointment with no less than £859.42 million spent on incomings.

And while we're well aware that all that spending hasn't translated into Champions League success, how have City's signings under Guardiola fared across the board?

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Extravagant transfer spending

Well, to get to the bottom of that question, we decided to rank all 21 major signings that City have secured with Guardiola in their technical area by how well they've performed in the sky blue jersey.

Now, it's worth noting that said 21 players don't quite add up to the magical £859m, but we didn't want to bore you with reams of youth signings who haven't even played for the first-team.

But with the major signings still adding up to more than £700 million, depending on how exactly you source your transfer fees, there are still plenty of expensive purchases for us to scrutinise.

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Ranking Guardiola's signings

So, disclaimers aside, check out how we think Guardiola's City signings stack up down below:

21. Philippe Sandler (£2.6 million)

The injured and forgotten Dutchman finishes rock bottom by default with a series of unfortunate circumstances meaning that he hasn't played a senior game for City since the 2018/19 season.

20. Nolito (£13.8 million)

One of very few unadulterated transfer clangers by Guardiola's City, Nolito never really settled in the Premier League and departed after just one season with only six goals in 30 outings.

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19. Angeliño (£5.4 million)

A fantastic player, of that there is no denying, but Angeliño never really got a fair crack of the whip in England and it's hard to place him when he only ever made 15 first-team appearances.

18. Nathan Ake (£40.0 million)

Having spent 105 days of his debut year on the treatment table, there's only so much we can judge at this stage but the early signs suggest that City might have paid over the odds for his services.

17. Danilo (£26.5 million)

For the money that City paid, Danilo offered them very little in return and it said everything that the Brazilian was moved on after just two seasons and 34 Premier League appearances.

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16. Zack Steffen (£7.0 million)

This feels a little cruel because, well, Steffen hasn't really put a foot wrong between the sticks for City, but there's only so much we can get excited about a goalkeeper purchased as back-up.

16. Claudio Bravo (£15.4 million)

A catastrophic 2016/17 campaign is outweighed by Bravo's service as a solid reserve shot-stopper, proving a penalty hero in the 2019 Community Shield and making a spectacular save in the 2020 Carabao Cup final.

15. Benjamin Mendy (£49.3 million)

Ugh, this is a frustrating one because Mendy has genuinely been superb at times when he's actually played, but it's hard to justify such a lofty fee for a full-back when injuries have plagued him so much.

Besides, it speaks volumes that Mendy averages a Premier League trophy for every 16.3 games he plays in the competition and has either been injured or ill no less than 16 times at the club.

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14. Ferran Torres (£20.8 million)

It's early days, so don't read too much into this lukewarm placement, but Torres has more given us flashes of what he might offer further down the line than consistently shining in his debut year.

13. Joao Cancelo (£60.0 million)

Hear me out because if Cancelo had signed for City last summer, then he'd undoubtedly be in the top five, but I can't ignore his woeful 2019/20 campaign that evens him out in the midsections here.

12. John Stones (£47.5 million)

Have I lost my mind?! No, I haven't, ladies and gentlemen, because as much as I've been delighted to see Stones thrive this season, I've got to take into consideration his City career as a whole.

And with his time in Manchester declining to the extent he was almost sold at one point, it makes sense to me that those difficult years even out what has undoubtedly been a world-class 2020/21.

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11. Oleksandr Zinchenko (£1.7 million)

A thoroughly underrated purchase in the Guardiola catalogue, it's fair to say that City have got value for money from a player who's amassed 41 appearances in Premier League title-winning years.

10. Leroy Sané (£37.0 million)

Unplayable in fits and bursts, frustrated and injured for long spells, there is more good than bad to say about Sane's time in England but it certainly leaves you wondering: what could have been?

9. Riyad Mahrez (£60.0 million)

Mahrez has never quite reached world-beating form in Manchester, but there's no getting away from his superb Champions League performances this season and overall contribution of 39 goals.

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8. Rodri (£62.8 million)

One of the best holding midfielders in the world, City were crying out for Rodri in the Champions League final because the Spaniard was born to play under Guardiola with his metronomic passing.

7. Aymeric Laporte (£57.0 million)

A crucial mid-season signing that set City on the war path for their 2017/18 and 2018/19 titles, Laporte's role might have faded recently, but make no mistake about his importance to Guardiola.

6. Gabriel Jesus (£27.0 million)

Underrate Jesus at your peril because for all the pelters he gets on social media, you simply can't dismiss a 24-year-old striker with 82 goals in 195 games despite competing with Sergio Aguero.

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5. Bernardo Silva (£43.0 million)

An absolute magician in midfield, Silva was in Ballon d'Or contention for his dazzling 2018/19 season and although things have taken a step down since then, he remains an integral cog for Guardiola.

4. İlkay Gündoğan (£20.0 million)

What's there to say about Gündoğan that hasn't already been said? Whatever you ask of the German workhorse, you'll get in buckets and that happens to have been goals, goals, goals in 20201.

3. Kyle Walker (£45.0 million)

Make no mistake about it, Walker has been an absolute juggernaut at times for City and no more so than in a 2020/21 campaign where lesser players would have been gobbled up Cancelo's form.

The Englishman has, by all accounts, made for one of the most unsung and pound-for-pound impressive signings that Guardiola has made at City across 184 appearances.

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2. Ruben Dias (£60.2 million)

It's only been one season, but what a season it's been. Seldom has a centre-back ever made such an instant impact in the Premier League, ultimately making the difference in City's 2020/21 title win.

1. Ederson (£34.9 million)

The final piece in the City puzzle and for a bargain price at that. Ederson is one of the world's best goalkeepers with three Premier League titles and two Golden Gloves in four years to show for it.

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Good signings on the whole

Across the board, you've got to say that City have enjoyed far more success than they haven't in the transfer window, even if it's cost them almost £1 billion to say so.

And that's where most of the City skeptics stand because although so many of the players have actually delivered the goods, it's come at a mind-boggling cost to the Citizen's coffers.

Sure, that's counterbalanced by three Premier League titles and more domestic honours than sense, but that oh-so desirable Champions League trophy remains out of reach.

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It just goes to show that there isn't an offer, no matter how lucrative, you could write on a cheque that would ever guarantee success in club football's biggest competition of all.