Manchester United have seen just five permanent managers since the formation of the Premier League in 1992 but plenty of players have come and gone.

It’s those that we’re going to be focussing on in this list as we whittle the many down to the few and look at the Red Devils’ 20 worst signings of the Premier League era.

Here we go…

Morgan Schneiderlin

First up is a midfielder who you may have forgotten even plied his trade at Old Trafford – current Everton and ex-France man Morgan Schneiderlin.

United tried to follow in the footsteps of their rivals Liverpool by poaching some talent from Southampton when they paid an eye-watering £25m for Schneiderlin in the Louis van Gaal era, but unlike the Sadio Manes and Virgil van Dijks, this Saints star was to flop at a much bigger side.

William Prunier

How could we leave Willian Prunier off this list?

When he was on the field Sir Alex Ferguson’s Red Devils would have been no worse off with an actual prune in central defence.

The former French international, somehow, is widely regarded as one of the worst players to ever ply his trade at “The Theatre of Dreams” and he’s now managing in France’s fifth tier.

Gabriel Obertan

Signing Gabriel Obertan for his all-star Old Trafford team and spending actual money on him too, at least they didn’t pay anything for on-loan Prunier, was hardly one of the Fergie’s masterstrokes – and it’s not the first time you will see the legend get his recruitment woefully wrong in this list.

The hapless winger Obertan made just 27 appearances in his four-year United career, scoring a mere one goal and only registering four assists, he did get a Premier League winners’ medal though.

Radamel Falcao

Radamel Falcao was hardly the first player to come to England with a huge reputation in European football and prove he’s not even near English top-flight standard, and he surely won’t be the last either.

Having scored bags of goals on the continent for the likes of Porto, Atletico Madrid and a resurgent Monaco team, the Colombian was given his big chance to shine in the Premier League on loan in Manchester for the 2014/2015 season.

Needless to say that he didn’t take it with the striker finding the back of the net on four occasions and he even got another opportunity with Chelsea the campaign after, to show everyone once again how below-par he is in England.

Zoran Tosic

The picture above rather sums up Zoran Tosic’s time in west Manchester – the Serbian was surrounded by some wonderful players such as Michael Owen, Paul Scholes, Rio Ferdinand and more and he was somewhat the odd one out.

This was because, like so many in this list, Tosic simply never had the ability to be a star at the world’s biggest club and that’s why he lasted only one term after joining from Partizan Belgrade in 2009.

Wilfried Zaha

Manchester United may well now regret letting go of Wilfried Zaha for well under £10m just four years go, however, this doesn’t take away from the fact that he wasn’t good enough for them.

£10.58m plus add-ons was a lot of money back in January 2013 and that’s exactly what David Moyes paid to capture him from Crystal Palace only for the Ivory Coast international to appear on four unmemorable occasions – now Zaha is once again knocking on the door of a move to a “Big Six” side having come on leaps and bounds since then.

Memphis Depay

Louis van Gaal should have been more cautious knowing how many attackers purchased from his native Netherlands have struggled to adapt in England after thriving over there.

Look up Dutch Premier League flops in the dictionary and Depay’s name will appear.

Massimo Taibi

Few members of this list have an iconic moment in a Man United shirt to their name, although we must confess Massimo Taibi’s is seminal for the wrong reasons.

Having impressed on his debut against Liverpool following replacing Peter Schmeichel in the summer of 1999, the Italian let Matt Le Tissier score with one of the tamest efforts in Premier League history against Southampton a game later and barely featured again – shocking.

Angel Di Maria

It’s hard to overlook our next United failure when it comes to the title of the biggest club-record signing dud in world football ever, Angel Di Maria.

To be fair to the Argentian though, he’s since shown his true quality at Paris Saint-Germain.

However, under the weight of a ridiculous £59.7m transfer from Real Madrid ahead of the 2014/2015 term, the Argentina great failed to make himself worthy of the famous Red Devils number seven shirt, providing little more than an eye-catching lob way at Leicester City.

Diego Forlan

A case of De Ja Vu here with Di Maria’s fellow South American Diego Forlan, a player that seemed to do extremely well at pretty much every club in his career apart from Man United.

Forlan was so bad at Old Trafford at times that it was laughable as he somehow managed to rack up close to a century of matches under Fergie who probably didn’t want to lose face after splashing out £6.9m on him, a large sum of money in 2002 football.