6. 2013/14

Photo by Paul Thomas/Getty Images

Notable Transfers: RB Guillermo Varela, CM Marouane Fellaini, AM Juan Mata

Notable Exits: LB Fabio

The beginning seems like a nice place to start, but in actuality it was anything but nice.

Like Sir Alex Ferguson, 2013 was Manchester United’s first season without long time Chief Executive David Gill. His replacement, Ed Woodward, would be taking over the club with full control over transfers.

David Moyes has claimed that deals were in the works for some of the game’s best, namely Cristiano Ronaldo and Gareth Bale (Hah!), but instead United settled for Marouane Fellaini and Guillermo Varela... That’s right, a modest £30m spent on a young full-back and a midfielder who can win headers and that’s it. Hopes would have been a lot lower had anyone seen what was to come, a complete Evertonization of United which resulted in a 7th place finish, no European football, and another manager search just a year on from Moyes’ appointment.

One deal that showed some promise was the arrival of Juan Mata in the January window. Unfortunately he made very little impact in his first season, and couldn’t save United in the race for European spots. Mata is the only transfer from that season still at the club, and played a big part in United’s few triumphs post-SAF.

This window set the tone for what was to come under Woodward, and is rightfully in last place for his inaction and poor footballing vision. A squad that won the league in record time the year before sank to its worst season in decades on his watch, and he offered very little to improve it.

5. 2018/19

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Notable Transfers: RB Diogo Dalot, CM Fred, GK Lee Grant

Notable Exits: CM Michael Carrick (retired), CB/LB Daley Blind, CM Marouane Fellaini

This season should be fresh on the mind, and the transfer performance, or lack thereof, by Ed Woodward was a popular narrative throughout. Only 3 players were brought in, and only one of them seemed to make sense. Dalot brought some much needed pace to the right back position, though his defensive quality is lacking. Fred cost around £50m, but hardly made any sort of impact. Lee Grant has made one appearance off the bench for United, and seems like a cool person.

United needed reinforcements after an unimpressive 2nd place finish, miles behind winners Manchester City, but instead Woodward and Mourinho chose this moment to do what they always do. Woodward stalled out of potential deals for key centre backs, Mourinho divided the dressing room and publicly challenged players and the board, and the resulting fallout was predictable.

Unfortunately, Woodward didn’t face the same fate as Mourinho, and is still in charge of the club’s transfer business despite supposed talks of creating a Director of Football position, or even a transfer board. Yet another low point in the history of the club.

4. 2014/15

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Notable Transfers: GK Victor Valdes, CB Marcos Rojo, CB/LB Daley Blind, CM Ander Herrera, AM Angel Di Maria, ST Radamel Falcao

Notable Exits: CB Rio Ferdinand, CB Nemanja Vidić, LB Patrice Evra, LB Alex Buttner, CM Anderson, AM Shinji Kagawa, RW/ST Wilfried Zaha, ST Danny Welbeck

This transfer window wasn’t just poor for the players that came in, a judgement made largely in hindsight, but for the players that left and were not replaced.

Rio Ferdinand, Nemanja Vidić, and Patrice Evra were the core group of a defense that dominated the Premier League for the better part of 8 seasons. They were essentially told by David Moyes they weren’t good enough to stay, and the three left for almost nothing. While Rio tailed off very soon after, Vidić and Evra went to Italy, where they each had something left in the tank. Evra in particular found success at Juventus, even playing in another Champions League final. Anderson and Buttner may not have shown much at United, and Kagawa and Welbeck were deemed not good enough by Louis Van Gaal. Zaha, however, wasn’t even given a chance by Moyes or Van Gaal. He went back to Crystal Palace and became a really good player, and is now reportedly of interest to several top clubs.

Though Di Maria and Falcao were both ambitious additions to the attack, neither made significant contributions to the team. Di Maria was a big flop because of the massive £60m fee, and the obvious lack of commitment from him. He was shipped out after just one season for a £20m loss on his fee. Falcao was only at United on loan, but the £6m loan fee + his wages was no small cost for the club.

Ander Herrera is the only player from this haul that worked out. 1 player from 6, and now he’s leaving for free this summer, yet another knock against Woodward.

3. 2015/16

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Notable Transfers: GK Sergio Romero, RB/LB Matteo Darmian, CM Bastian Schweinsteiger, CM Morgan Schneiderlin, LW Memphis Depay, FW Anthony Martial

Notable Exits: RB Rafael, CM Tom Cleverley, AM Angel Di Maria, LW Nani, ST Javier Hernandez, ST Robin Van Persie

This window featured an attempt to lock down holding midfield and relieve some of the pressure on Michael Carrick, but the result was one of the most boring seasons in recent memory. Louis Van Gaal’s possession based tactics became even more conservative in his second season with his new “Schmidfield,” and in a year where the top 6 was pretty mediocre across the board, Leicester City found themselves on top after an incredible campaign. With Arsenal and Tottenham as the closest title rivals, United had to settle for the FA Cup and yet another year of failing to qualify for the Champions League. They were even in the mix at the top until a disastrous December/winter period put them towards the back of the pack. In hindsight, this was an enormous opportunity missed by Manchester United to get back on top in English football.

This window might have been in contention for worst with the last two if not for Anthony Martial, but even his growth has stunted a bit. Martial did give Wayne Rooney some much needed help in the goal-scoring department, and carried the team along with Marcus Rashford to the end of the season and to FA Cup glory. Memphis Depay put on a couple crowd-pleasing performances, but ultimately didn’t live up to the no. 7 shirt.

Another negative of this window is the number of significant departures. Nani, Chicharito, and Van Persie were major contributors for United at one point. Though they had fallen off a bit, their production was not adequately replaced. Angel Di Maria as well only further damaged United’s reputation when he was sold off only a year after becoming the club’s record signing. Woodward’s mistakes were mounting, and it was becoming clearer and clearer there was no overall transfer strategy at the club other than pursuing what the manager suggests.

2. 2017/18

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Notable Transfers: CB Victor Lindelöf, CDM Nemanja Matić, LW Alexis Sánchez, Romelu Lukaku

Notable Exits: RB Guillermo Varela, AM Henrikh Mkhitaryan, AM Adnan Januzaj, ST Wayne Rooney, ST Zlatan Ibrahimović

This one is 2nd because one of them had to be. This transfer window is could very well become another massive flop, and already sort of is, but it’s up here for for now because of A: The horror show you’ve read about already, and B: There have been some (emphasis on “some”) decent contributions from the arrivals.

Zlatan Ibrahimović’s debut campaign at Old Trafford was remarkable, but had to be replaced after the Swede’s knee injury in the Europa League quarterfinal. Romelu Lukaku came in and did exactly that to start the 2017/18 campaign. Nemanja Matić similarly seemed to fit right into the midfield, and United and City quickly separated from the rest of the pack. Then, the season turned quickly around the start of the winter fixtures. Losses and draws added up to give City acres of space at the top of the table, and the poor form and infighting that would eventually lead to José Mourinho’s dismissal began for United.

Now, Lukaku’s scoring has slowed down, and Matić’s legs are all but gone. Victor Lindelöf has developed nicely, however, despite having hardly any help at the back.

And, of course, there is the case of Alexis Sánchez. The swap deal in January, 2018 seemed like a nice idea at the time as Henrikh Mkhitaryan had ceased producing and United lacked exciting attacking talent. Alexis had a couple decent performances, but for the most part disappointed in his first half-season. Now, after his first full-season, he is probably the biggest transfer bust in the history of the club. He is one of the highest paid footballers of all time, but has done nothing.

Finally, the exits again stick out: Zlatan Ibrahimović and Wayne Rooney. I don’t think anyone would argue Rooney or Zlatan would’ve had much left to contribute production-wise. Despite both of them taking the MLS by storm, Zlatan’s injuries and Rooney’s decline made each of them obsolete for United by the time they left. Moving on was the right decision, but not replacing their leadership or the production they once contributed has backfired.

1. 2016/17

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Notable Transfers: CB Eric Bailly, CM Paul Pogba, AM Henrikh Mkhitaryan, ST Zlatan Ibrahimović

Notable Exits: CM Morgan Schneiderlin, LW Memphis Depay

The winner, by default.

This was probably the most exciting transfer window (at the time it was happening) from the Ed Woodward era as well as the most successful. Bailly and Mkhitaryan were locked up early in the summer, and then came Zlatan Ibrahimović on a free transfer. Mkhitaryan was Bundesliga Player of the Year in 2015/16, and Ibrahimović had just finished up a contract at PSG which he spent putting them on the map. The rest of the summer was spent in limbo over Paul Pogba’s return, and the deal, at the time, was a world record transfer.

2016/17 also saw more silverware to follow up on the 15/16 FA Cup campaign, and both the Europa League and League Cup runs featured some exciting performances from the new signings. Zlatan Ibrahimović in particular was a huge boost to both the team’s performances and fan morale. He is by far the best signing of the Woodward era from a quality standpoint, but due to injuries he wasn’t able to keep up the good work.

By the end of this season it seemed as though every one of the transfers had been a good move, but the moves have since come into question. Mkhitaryan was given up on by Mourinho rather quickly in January 2018, and Eric Bailly’s promising growth suddenly evaporated in the 2018/19 season. Zlatan moved to LA Galaxy after a slow recovery kept him out of the squad for most of 2017/18, and Pogba seems ready to move on this summer rather than continue to build on 3 solid seasons at Old Trafford.

The ambition of the 16/17 window has not been replicated, which is part of the reason why it has become a bit of a failure despite the tremendous initial impact (and it’s #1 spot on this list). United’s lack of overall strategy, poor recruitment, and bad management has led to the club missing out on a lot of talent, and mismanaging some as well. The squad became a combination of players brought in by 4 different managers, each with different philosophies and demands, and for the most part is has not worked. The most convincing members of the team are De Gea, who was brought in by Sir Alex and wants to leave, Lindelof, who has no help, Pogba, who wants to leave, and Rashford, who is an Academy product.