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How Roy Keane’s bittersweet ‘finest hour’ helped Man United achieve the impossible

It’s seems ridiculous now, but there was a time when Sir Alex Ferguson’s powers in European competition were questioned.

He wasn’t considered a ‘fraud’ or anything as extreme as that.

It’s just that prior to 1999, Fergie’s Man United had enjoyed sustained domestic success without the equivalent dominance in Europe.

Until one memorable season…

For the fourth edition of our HISTORY LESSONS series, I re-watched the full 90 minutes of the semi-final second leg between Juventus and Man United in Turin.

A night to remember

A night to remember

Why this game?

Everyone knows about Ole Gunnar Solskjaer’s winner against Bayern Munich in the final, but the last-four showdown against Italy’s Old Lady was the most poignant stage of the campaign.

Juventus had featured in three consecutive Champions League finals and were considered the street-smart experts of elite knockout football.

This video of Gary Neville’s reaction as he finds out Juve have qualified for the knockout stages says everything you need to know about their fear factor at the time.

After a 1-1 draw in the first leg at Old Trafford, Ferguson’s troops faced the unenviable task of resisting Juventus in their lair.

Something they failed at the previous season when they lost 1-0 at the Stadio Delle Alpi to a late Filippo Inzaghi goal.

Which brings us neatly onto the game itself…

Good to see Antonio Conte in the mix

Good to see Antonio Conte in the mix

Ryan Giggs’ injury was the big talking point before kick-off

Ryan Giggs’ injury was the big talking point before kick-off

The hosts start strongly as Zinedine Zidane works a short corner before finding Inzaghi at the back post with a whipped cross.

The predatory poacher stubs home in trademark fashion despite some close attention from Neville.

You have to wonder what the Sky Sports pundit would have made of his past self’s defending: he hasn’t even got eyes on the ball!

Four minutes later, Inzaghi doubles his tally and Juve’s lead, benefiting from a deflection off Jaap Stam that gives Peter Schmeichel no chance.

Both goals are typical of the Italian; instinctive and blessed with the kind of luck that only lingers around a player who has devoted their life to the act of scoring goals.

The man they called Pippo was a curious player.

Ferguson famously said of him: “That lad must have been born offside.”

Inzaghi spends a third of this game testing the linesman’s attention, a third throwing himself to the floor, and a third making genius runs in behind.

One of a kind

One of a kind

And so United find themselves 2-0 down (3-1 on aggregate) to a team seen as invincible over two legs.

As the game restarts, Ron Atkinson on commentary gravely describes Juve as: “The last team in the world you want to concede two goals to.”

Up steps Roy Keane.

For many United fans, this famous night in Turin is the Irishman’s finest hour.

There’s a video on the club’s official website which is just every one of Keane’s touches.

Watching it back, I have to say I think memories have been embellished slightly.

Defining performance

Defining performance

United’s captain is excellent – his composure on the ball and progressive passing is exceptional – but he does not dominate the game in the way the mythology around this performance suggests.

17 minutes in, Keane implants his studs into Edgar Davids’ ankle — the Dutchman was majestic in the first leg but shows little interest after Keane’s reducer.

Not long after, David Beckham swings a corner to the near post and Keane meets it with desire, authority and skill to expertly guide the ball into the far corner.

United would repeat this goal almost exactly in the final with Teddy Sheringham taking Keane’s place and Solskjaer making sure under the crossbar.

Clive Tyldesley describes the goal as a ‘captain’s goal’ and while this is an overused cliche in football, it is fitting on this occasion.

As sweet a glancing header as you’ll ever see

As sweet a glancing header as you’ll ever see

United are instantly energised by Keane’s goal, almost as if the hosts’ aura evaporated the moment the ball diverted off the skipper’s forehead.

Then comes the moment that makes Keane a legendary martyr.

Jesper Blomqvist’s slack pass makes life difficult for Keane and allows Zidane to gain possession in midfield.

Sensing danger, Keane lunges at the gifted Frenchman and brings him down to concede a free-kick, and a yellow card too.

This booking means he is suspended for the final.

A moment of historical symmetry: Paul Gascoigne was booked at the exact same stadium in the 1990 World Cup semi-final.

Gazza teared up within seconds, realising he would have to sit out of the final if England made it through.

Keane’s reaction is noticeably different.

My lip-reading isn’t great but he quite clearly yells at Blomqvist: “What the f*ck was that ball?”

You can even see his Irish accent.

Decisive moment

Getty - Contributor
Decisive moment

The most significant difference between Keane and Gazza’s Turin bookings is that the latter’s suspension never materialised due to his side’s elimination, whereas the former was forced to serve his after a bittersweet victory.

In a midfield that also includes Davids, Zidane and Beckham, Keane has the greatest gravity about him and this is what the fans rightfully remember.

This is far from a one-man performance though.

After a quiet start, Dwight Yorke and Andy Cole’s telepathy becomes apparent.

Charged up by Keane’s header, the visitors strike again when Cole finds Yorke with delicate cross and the latter makes no mistake with his close-range header.

2-2 on the night, United going through on away goals…



Watching with hindsight, there are some charming reminders of how the game has changed in the last 20 years.

The commentators are critical of ‘cavalier’ Denis Irwin for momentarily taking up an advanced position Andrew Robertson would consider conservative.

At half-time, Ferguson gives a brief interview to ITV in which he reveals little and shows no interest in Juventus’ imminent substitution.

After the restart, centre-back Ciro Ferrara pushes Cole in the face with some force — a blatant red card these days.

The referee reluctantly trots over and tells the pair of them to cut out the handbags, not even threatening a yellow.

As the game enters the last half hour, the lottery numbers flash up at the bottom of the screen

As the game enters the last half hour, the lottery numbers flash up at the bottom of the screen

Perhaps the most pleasing nostalgic element is Yorke and Cole’s partnership.

In 2019, most elite teams deploy a lone striker or a dynamic front three, but back in 1999 the default was 4-4-2.

Having already combined for the equaliser, the pair ensure progression in the 84th minute when Yorke latches onto a big punt up field from Schmeichel and engineers a one-on-one scenario.

He rounds the keeper and is brought down for a stonewall penalty… but the referee is spared the decision as Cole follows up to tap the ball into the empty net.

3-2 on the night, an away goal cushion, job done.

Victory sealed

Victory sealed

Ferguson celebrated with champagne on the flight home, deservedly savouring a famous victory.

He would be without the talismanic Keane for the final – and Paul Scholes who was fatally booked for a typically Scholes two-footed challenge on Didier Deschamps – but the win had worked a miracle for his side’s morale.

If they could beat Juve in Turin after going 2-0 down in the first ten minutes, they could beat Bayern Munich in Barcelona, even if they needed two goals in stoppage time.

Bottoms up

Bottoms up

United used this victory to fuel the first ever treble by an English side — an achievement that remains unmatched today.

1998/99 will forever bet the crowning moment of Ferguson’s distinguished career, one that evidences his status as the greatest club manager of all time.

Chelsea, Arsenal, Liverpool and Man City have all boasted brilliant teams since 1999, but none have matched United’s treble-winning campaign.

20 years later, it is still the yardstick by which all great English sides are measured.


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Drink it in, Gareth

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