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Retro Diary: Middlesbrough vs Manchester United

In the run in to Premier League and Champions League double, United start to tire

Middlesbrough v Manchester United Photo by Matthew Peters/Manchester United via Getty Images

Last week we fired up the retro diary to look back at Manchester United’s trip to Rome in the 2008 Champions League quarter-final. As I alluded to at the end, three days later United faced a Premier League trip to 13th placed Middlesbrough and that would be an intriguing match to look back on.

United had faced Roma on Tuesday, Boro on Saturday, and then were home to Roma the following Wednesday before welcoming 3rd placed Arsenal to Old Trafford on Sunday. A win at the Riverside would put them five points ahead of Chelsea. This was a crucial point of United’s season and this specifically would become a crucial game in shaping how United approached the rest of the season.

Let’s have a look back at it.


Black kits! Love it. One of the best kits United ever had. A pity they didn’t wear these more often.

Team news. That’s Adam Johnson on the bench! Amazing how many people in this game would end up at Sunderland at some point in their career.

United are back into their typical 4-4-2 that they used domestically. Remember last week when I kept wondering how Anderson got the call in Rome instead of Owen Hargreaves? Eventually I figured it was just rotations to keep someone, in this case Hargreaves, fresh for the weekend. Nope. Hargreaves and Anderson to the bench, Paul Scholes and Michael Carrick keep their places.

Nemanja Vidić picked up an injury midweek, and was replaced by John O’Shea. Found it interesting that when that happened Wes Brown, a natural center back who had been playing right-back all season, didn’t move back to the middle and have O’Shea play on the outside. Same lineup here so I’m thinking there’s some tactical/continuity reasons behind it.


1st Minute:

Right off the kickoff Boro get the ball back to their keeper and Carlos Tevez immediately sprints back onto defense. This team was more than happy to let you walk the ball up the pitch. They wanted you to. Ferguson’s attacking football, am I right?!!

2nd Minute:

Whoa, things are getting weird formational-y right away. Ryan Giggs has tucked inside to form a midfield three.

This can happen as players move around a bit, especially when they have the freedom that this United team had, but this is a pretty structured midfield three.

As United advance the ball, it becomes clear this isn’t just an accident. Giggs pushes even further up, and into the middle to what is essentially the number 10 role. Wayne Rooney is the only player even somewhat giving width down that left side.

After a few minutes it becomes clear this is how United are going to be playing. It’s kind of a 4-4-2, but a really imbalanced one. It pretty much looks like this.

It’s kind of insane. United are just completely neglecting the left hand side of the pitch, especially in midfield. Occasionally Patrice Evra will push up, but when United lose the ball that just puts more pressure on what’s become a back three of Brown, Rio Ferdinand, and O’Shea. It’s making this a wide open game.

9th Minute:

Peak Carrick was just so good. He really wasn’t appreciated enough.

11th Minute:

United get their goal and immediately fall into a 4-5-1, or a 4-4-1-1. Whatever it is it’s really narrow. That midfield trident is entirely on the left side of the pitch.

This is how United play. They rely heavily on the individual skill of players. They sit back and will let you have the ball, until someone tries to make a play on it. If that player wins it back they can go on the break, and when they break, oh do they do it quickly.

13th Minute:

But here’s the problem with relying on individual talent. The defense is very unstructured. Boro get the ball deep and look at this.

There’s three attackers and three defenders and somehow United are completely outnumbered. Evra goes to help out Giggs, then just essentially abandons the play (taking up a central midfield position when the midfielders have dropped into the box)? Scholes completely over-commits to the second man, taking himself out of the play. Giggs just leaves the runner to go inside and pick up the man that Evra left free, then has to switch over to the man Scholes left free, only to then have to make a last ditch effort on his initial man whom he left completely free.

It’s horrific defending but it works because: individual talent.

15th Minute:


We get our first look at the now-England manager back in the day and immediately the commentator Jon Champion starts talking about Southgate’s recent quote about Middlesbrough’s form:

“Interesting point that he made pre-kickoff. Despite the fact that they’re lower in the table this year, he feels that they’re a better team than they were last year.”

Gareth! You’re like 10 years too early to have that kind of thinking! Truly a man before his time.

Immediately the color commentator responded:

“Well I’d argue that point with him. If they finish below where they finished last year with less goals scored, fewer conceded, and less points then they’re not are they?”

Phew, we’re back to 2008.

22nd Minute:

This has somehow simultaneously been a back and forth match and one where nothing is really happening.

When United don’t hit Boro on the break, they’re really struggling to break Boro down. This is starting to look like 2019-20!

22nd Minute:

The defensive positioning god. As good as this team was, if we were watching them today we’d be pulling our hair out. It’s terrible.

Scholes comes right on over next to Carrick. Why? I don’t know. He’s not closing the man down, he’s just next to Carrick and leaving the middle of the pitch WIDE open.

Boro simply play the ball into that space, which in turn forces O’Shea to step out. Boro’s striker then makes a run right into the space vacated by O’Shea leading to a good chance and forcing an excellent save by Edwin van der Sar — who crucially read what was happening right away to get into a great position for the save. Again, individual talent.

(This Southgate guy may know what he’s doing).

25th Minute:

Do Boro not have any attackers who can play on the right side? United are still completely ignoring their left side. Giggs and Rooney have moved centrally. The only time anyone pops up on the left side of the pitch is if the ball is there.

28th Minute:

This team’s ability to immediately launch a break remains unparalleled.

The only issue today has been United stalling while on the break, giving Boro time to get back. It’s becoming a bigger issue as the game goes on as United continue to struggle to break them down.

29th Minute:

Speaking of. As Sir Alex Ferguson always said, when you’re looking to launch a counter attack the first pass is so crucial. A great example of it right here.

This is why in modern defenders who can play the ball with their feet are so valued. With one touch Rio Ferdinand clears a ball from danger and gets it to Carrick, who can launch a break with just a single pass.

29th Minute:

God, even when he didn’t score young Ronaldo was SO. MUCH. FUN.

34th Minute:

That loosy-goosy defending and ignoring comes back to bite United.

Giggs sorta half-asses closing down the initial man. Everyone in this play is covered pretty well, but also not covered at all. Nonetheless Boro do a good job of catching United out.

44th Minute:

Hey check out Carrick getting forward!

And another great example of the individual IQ from everyone on this team. Carrick goes forward, and when he loses the ball, Tevez recognizes the gap and sprints to get back. Scholes fills in for Carrick, Evra shifts in to the midfield. The one problem with all this movement is...

What if you don’t win the ball back?

Now United are caught out and it’s Tevez hustling back to cause a bad touch and let the ball be won back by...Rooney.

The work-rate of these two strikers is nothing short of sensational but man, this is a really inefficient way of playing.


Been a very entertaining game so far. United as always are tons of fun to watch. Their openness helps with that. Tactically though Boro have by far been the better team, and if they were any good at all they’d have punished United for their countless errors so far.

Second Half

The second half begins with O’Shea moving to right-back and Brown going to the middle. There have hardly been any “oh my god O’Shea what are you doing” moments but this change definitely felt necessary.

52nd Minute:

A great look into the differences between old school defending and modern defending. First we’ll look at this play from John O’Shea in the first half.

United under pressure, O’Shea gets the ball and just hoofs it down the field. What does that do? Pretty much nothing. It goes right to Middlesbrough who can launch another attack.

Now, here’s Rio Ferdinand in the second half.

Rio came up as a midfielder but was moved back to central defense while at West Ham and this is why. He does a great job with the initial defending, then holding control of the ball until he can pick out a pass to his teammate. United retain possession and can launch an attack, rather than just giving the ball back to Middlesbrough.

Being comfortable playing with your feet is crucial for modern center backs. It’s why Carrick would be a central defender if he was coming through the ranks now.

52nd Minute:

It will never stop being amazing how quickly this United team (read: Ronaldo) can go from nothing to being really dangerous. One throw from Van Der Sar and Ronaldo is on the break.

56th Minute:

The lazy defending continues and once again Boro make United pay. Anyone want to stick with that runner at all? Looking at you, Carrick.

Things aren’t looking great for United here. Boro now have a lead and will be able to sit deep and defend, which can be problematic for the Reds considering they’ve been struggling to break Boro down all match.

59th Minute:

Boro are not sitting back! They’re not stopping!

Rio Ferdinand has been an absolute beast all game. Remember when I said John O’Shea had been super terrible? Well that’s because Ferdinand bailed him out about 100 times in the first half.

It’s incredible how easy United keep getting cut open. This starts when Rooney tries to play a one touch pass to... probably Carrick but not really anyone. United were looking to break on the initial pass, which meant everyone started getting forward, including Patrice Evra.

That leaves all that space available on the wing and Wes Brown, who’s barely even in the frame, is the man responsible for getting over. United are either making this really easy for Middlesbrough, or Boro’s manager has studied United and knows exactly where to exploit.

(Thinks about who Boro’s manager is again...)

60th Minute:

The commentator starts talking about how Ferdinand hasn’t stopped limping since making that stop. He’s really struggling. Again, Ferdinand has been a complete beast all game. This could be a problem.

63rd Minute:

United are going to make a sub and it’s not for the injured Ferdinand. Carlos Tevez comes off, Ji-Sung Park comes on.

Park? Down a goal with just under a half hour to play and we’re taking off a striker for Park? I know the other bench options (Anderson, Hargreaves, Gerard Pique) aren’t much better but really?

This seemed weird to me in 2008 and it seems weird to me now.

Park slots in on the right with Ronaldo moving up top allowing United to keep playing their weird 4-4-2 with Giggs being the nominal left winger but actually playing centrally. Or Rooney is drifting out wide, and it’s a 4-5-1. Still, interesting decision when you’re chasing the game.

65th Minute:

Second sub. Hargreaves comes in at right back for O’Shea. Very attacking sub.

69th Minute:

Third sub. Ferdinand finally comes off. Pique is on. If Boro keep attacking this will get dicy.

73rd Minute:

United finally get their breakthrough and of course, it’s Park with the assist. Just like last week when I made snarky comments about O’Shea and he ended up being the catalyst for the first United goal vs. Roma. I wish Andreas Pereira would react to my snarky comments like this.

What a fantastic ball from Carrick to get this started. This is why we should have second assists in football like they do in hockey. This goal doesn’t happen without Carrick.

This is what United have been lacking this year. None of their midfielders make passes like this.

Well, none except for...

77th Minute:

Boro make their first change. Striker Afonso Alves, who scored both goals, comes off as Southgate brings on a fifth midfielder. Southgate has decided that one point is enough.

This is where Ferguson shines. I’ve spoken about this before and how it plays right into Fergie’s hands. United can now send an extra player forward because they have one fewer player to worry about coming back the other way.

85th Minute:

And here it happens. Ronaldo with the ball on the left side going against two defenders and drawing a foul. That’s not the important part here. Take a look at right-back Owen Hargreaves and where he is at the start of the clip, and where he is at the end. United are throwing everyone forward.

88th Minute:

Very interesting sequence here. United get a great chance on one end with everyone forward. Boro get the ball with a great chance to break. They don’t, and Brown plays it harmlessly back to van der Sar.

Then van der Sar completely fluffs his pass and look, there are STILL no United players back, nor trying to get back.

Once the pass is muffed, some players (Evra, Hargreaves) start to hustle back, but Boro essentially get a free attack that ends with Pique blocking a shot.

You know what that says? United are tired.

Full Time

The game ends in a 2-2 draw which turns out to be a pivotal moment for United. They’re outshot by Middlesbrough 15-12 on the heels of being outshot by Roma a few days earlier. Over the next week they face Roma again and then have a huge clash with Arsenal at the weekend. They’re three points ahead of Chelsea with five games to play.

This team had been running freely over every team they faced all season but after this match Ferguson realized that had to change. They were tired. Rooney and Tevez running all through the midfield and the midfielders freely getting up and back had taken its toll. Things needed to change.

And so, gone was the free running football United had played all year — it would only come back once, in their final home game, a 4-1 win over West Ham. United began hunkering down defensively, picking their spots when to attack, and relying on their stars to produce moments of brilliance.

Their possession dropped over the last six weeks. They grinded out a 1-0 win against Roma. They were out-possessed and out-shot at home to Arsenal a week later, winning on a Ronaldo penalty and that Owen Hargreaves free kick — set pieces. They were badly out-possessed by Barcelona in both legs of the Champions League semifinal, winning 1-0 on aggregate thanks to that spectacular Scholes goal.

They won just three of their final six games, but you know what? It worked. They pulled out the title and won the Champions League. They spent 85% of the season mesmerizing us with tremendous football and then hunkered down when they needed to.

This game was a wake up call for Ferguson. He realized his team couldn’t close out the season at that high level. If they wanted to win the title they were going to have to back off the throttle a bit. They did. It worked.