Ranking Man United's two worst and two best summer transfer windows

Matt Jones - Editor 09:20 19/06/2019
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There have been some tough times for Manchester United fans since Sir Alex Ferguson delivered a 20th Premier League title to bring the curtain down on his glorious 27-year reign at Old Trafford in 2012/13.

In the ensuing six seasons, the club has hired four managers and fired three of them, while the wait for title No21 seems like it will go on for a few more years. Jose Mourinho’s sacking last December yielded a brief upturn in fortunes, but the season ended in misery as a failure to finish in the Champions League places was compounded by Manchester City’s domestic treble and the fact Liverpool and Chelsea claimed European trophies, while even Tottenham and Arsenal made the finals.

Daniel James became the first signing of the Ole Gunnar Solskjaer era earlier this month, but a lot more transfer activity is expected.

So, ahead of what United desperately need to be a successful summer in the market, we take a look at their two worst and two best summer transfer windows during the Premier League era.


Dwight Yorke and Andy Cole


Signings: Jaap Stam (PSV, £10.75m), Jesper Blomqvist (Parma, £4.4m), John O’Shea (Waterford Bohemians, undisclosed), Dwight Yorke (Aston Villa, £12.6m)

Notts County goalkeeper Russell Best might well have been hoping he’d be the signing of the summer in 1998 when he arrived on a free from Notts County, but he ended up being blown away by the other players who joined him at Old Trafford.

Jaap Stam, Jesper Blomqvist, John O’Shea and Dwight Yorke all arrived and went on to play key parts in the greatest season in the club’s history as an unprecedented treble of Premier League, FA Cup and Champions League was acquired in thrilling fashion.

Stam was arguably United’s greatest defender of the Premier League era but a fallout with Ferguson curtailed his United career while Yorke was another to fall foul of the manager – even though his goalscoring exploits and lethal partnership with Andy Cole more than made up for his misgivings.

Yorke enjoyed his most productive season in his debut campaign with United, rocketing in 29 goals in 51 appearances.

Blomqvist’s role was more understated although he did feature in 38 games and started at the Camp Nou in the absence of Paul Scholes and Roy Keane as United stunned Bayern Munich. O’Shea, arriving as a 17-year-old, played no part in the treble-winning campaign and didn’t make his United debut until the following season, but became a firm fan favourite and even cult hero during 12 years at Old Trafford.

Van der Sar Terry


Signings: Edwin van der Sar (Fulham, undisclosed), Park Ji-sung (PSV, £4m), Ben Foster (Stoke City, undisclosed)

A veteran goalkeeper and trusted utility player hardly seem the most likely duo to form the basis of one of the most successful transfer windows in the Premier League era for United.

But the summer of 2005 proved to be the interconnecting component to what was the beginning of the final golden period of the Ferguson dynasty. After spending the best part of seven years searching for a suitable Peter Schmeichel replacement, Dutchman Van der Sar was signed from Fulham. His assured six-year stay helped erase a series of butter finger flops; Fabian Barthez, Massimo Taibi, Mark Bosnich, Roy Carroll, Tim Howard and Andy Goram.

Korean captain Park was a workhorse and always a man for the big occasion. Let’s not forget that two of the greatest United defenders in the Premier League era – Nemanja Vidic and Patrice Evra – followed them to Old Trafford in the January window.

Ferguson had tempted teenage sensation Wayne Rooney away from Everton the previous summer and then coaxed Michael Carrick from Tottenham the following year.

All of the new cogs combined to end a barren three-year wait for a league title in 2006/07, while a third European crown was hoisted in the Russian rain 12 months down the line.




The one signing of note cost just £1.2m, but the purchase of Eric Cantona was possibly the biggest transfer in United’s history. The enigmatic Frenchman spent just five years at Old Trafford but was the catalyst for change under Ferguson, inserting a style and swagger into a United side that won the league title for the first time in 26 years this season.


A year later and just a solitary signing, but just how significant Roy Keane’s arrival at United has been can probably never be fully appreciated.

A relative unknown, the Cork-born firebrand was snatched from under the nose of Kenny Dalglish and Blackburn Rovers – he had a gentleman’s agreement to join Rovers on Monday after the Blackburn office staff leaving early had scuppered his move from Nottingham Forest being made permanent the previous Friday.

Ferguson got wind of this and tracked Keane to Cork over the weekend. The rest is history, Keane signed for United for a then British record of £3.75 million.


Fellaini of Manchester United


Signings: Marouane Fellaini (Everton £27.5m), Guillermo Varela (Penarol, undisclosed), Saidy Janko (Zurich, undisclosed)

The greatest manager in club history had just departed. And Ferguson’s one last, great throw of the dice in prising Robin van Persie from Arsenal had gone a long way to United lifting the league title – their 20th in total. The Dutch hitman plundered 30 goals in 48 games in all competitions (his second best season tally) as he provided the spark for the great Scot’s final hurrah.

In came David Moyes, and the ‘Chosen One’ needed a strong start in the transfer market. Instead, he oversaw a catastrophic summer. One in which bids for Cesc Fabregas, Toni Kroos, Leighton Baines and Sami Khedira were all either rebuffed or inexplicably bungled.

His headline acquisition? Returning to Everton to sign Fellaini, although even this left Moyes with egg on his face as United forked out £27.5m when a clause in the Belgian’s Goodison Park contract ensured he could have joined any club that offered £23m for him before July 31.

Swiss youth prospect Janko made one solitary League Cup appearance for United and has since failed to find a home at Bolton Wanderers, Celtic, Barnsley, Saint-Etienne, Porto and Nottingham Forest. Varela, meanwhile, made a total of 11 appearances during four seasons at Old Trafford and now plays for FC Copenhagen.

Anthony Martial 3


Signings: Memphis Depay (PSV, £25m), Matteo Darmian (Torino, £12.7m), Bastian Schweinsteiger (Bayern Munich, £6.5m), Morgan Schneiderlin (Southampton, £25m), Sergio Romero (Unattached, free), Anthony Martial (Monaco, £36m)

If you had to pick from the above list of players, one who was going to enjoy a successful career in a red shirt, your guess would not have been free agent Sergio Romero, who didn’t cost a penny.

Everyone else was either a total flop, or underwhelming. Depay is an incredible talent but his immaturity destroyed any hope he had of adding his name to the prestigious list of previous iconic United No 7s. Schweinsteiger was stumbling into his twilight years and his ageing legs meant he was way past his prime, while Schneiderlin found the elite level too far beyond his capabilities.

Darmian has stepped up when called upon on various occasions but will not be missed by United fans when he, surely, eventually departs this summer. It’s hard to blame the Italian for his lack of star power, but there’s plenty of blame to lay at Martial’s door.

The 23-year-old is one of the most frustrating footballers to have ever entered through the Old Trafford doors. He has so much ability and attributes that, even now, he could still potentially become a world-class player.

But, for all his undeniable talent he is yet to catch fire and now, after four full seasons and 48 goals in 172 games, United fans are still yet to see the best of the flamboyant Frenchman, and wonder if they ever will.


Michael Owen City


Perhaps we’re being deliberately provocative here. After all, this is the summer United signed Cristiano Ronaldo. But, alongside the acquisition of the spotty-faced, spaghetti-haired Portuguese for £12.24m, United also brought in some utter donkeys.

David Bellion, Eric Djemba-Djemba and Kleberson remain some of the worst signings in United’s history. American goalkeeper Tim Howard was a moderate success but enjoyed his best days in England when he moved on to Everton.


Sticking with the Ronaldo theme and by the time he left England six years after his arrival, he was well on his way to being one of the greatest footballers ever.

He won his first Ballon d’Or while in a red shirt in 2008. Antonio Valencia has been a fine servant for United, but was hardly the stellar signing distraught United fans craved in the summer of 2009, with Ronaldo’s departure leaving them devastated as he headed for Real Madrid.

Also, in addition to the arrival of the Ecuadorian from Wigan, injury-prone former Liverpool strike Michael Owen was acquired as well as Gabriel Obertan and Mame Biram Diouf. Pitiful.

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