Liverpool v Osasuna - Pre-Season Friendly Official Premier League Nike Strike Aerowsculpt 21/22 during the pre-season friendly match between Liverpool FC and CA Osasuna at Anfield on August 9, 2021 in Liverpool, England. Liverpool England breton-liverpoo210809_npyDF PUBLICATIONxNOTxINxFRA Copyright: xJosexBretonx

As the eagerly anticipated Champions League final between Liverpool and Tottenham in Baku draws nearer, in this series Tale of Two Halves looks at classic European encounters of the past involving either side.

Whenever you think of Liverpool and the Champions League, many football fans will immediately associate them with 2005 and Istanbul.

The ups and downs of Liverpool’s capitulation in the first half, followed by redemption in the second half.

Not just the final – it was a remarkable campaign for all associated with the Reds.


Think back to Martin Tyler and Andy Gray’s unforgettable piece of commentary as Steven Gerrard fired Liverpool into the knockout stages having needed a last game win over Olympiacos.

Think back to that two-legged affair with Jose Mourinho’s all-conquering Chelsea side, when Luis Garcia tapped home the hugely controversial only goal of the tie.

And after all that, a final against Italian giants AC Milan looked a steep task even before kick off.

Liverpool needed to win – without success in Istanbul, they were set to play UEFA Cup football next season after a fifth-placed finish in the Premier League.

Milan still had the likes of Paolo Maldini and Gennaro Gattuso leading the team, with Andrea Pirlo pulling the strings from midfield.

It was to be Brazil legend Cafu’s final shot at European final glory – before his final World Cup a year later – whilst the side was spearheaded by Chelsea loanee Hernan Crespo and one of the best strikers in the world at the time, Andriy Shevchenko.

Up until the semi-finals, Milan had breezed past their competition, going through both knockout ties against Manchester United and Inter without conceding a goal.

There were signs, however, in the semi-final that they were beginning to come unstuck.

After a comfortable 2-0 win over PSV at the San Siro, they played their part in a manic finale at the Philips Stadion.

PSV led 2-0 going into added time, Ji-Sung Park and Philip Cocu’s strikes meaning the tie was set for extra time.

In the first minute added on to the 90, however, Massimo Ambrosini struck to break Dutch hearts and send Milan through to contest for their seventh European crown.

Cocu scored just a minute later to put the pressure back on Milan, but they saw through the remainder of the allotted time to scrape through on away goals.


It was the first time Rafael Benitez’s Liverpool side had reached the Champions League final since 1985 when they lost 1-0 to Juventus.

Milan hadn’t been away from Europe’s biggest stage for long, having beaten Juventus at Old Trafford just two years earlier in 2003 to record their sixth title.

There was controversy before the game, with Liverpool not guaranteed to be allowed to defend their title if they had won.

Of course, the usual UEFA protocol, and one that has been maintained ever since is that the winner of the Champions League is granted automatic qualification to the tournament for the next season, regardless of league position.

Liverpool wrote a written request to UEFA and were backed by both the FA and Milan manager Carlo Ancelotti.

Ancelotti had little to worry about on that front, Milan having finished second in Serie A that season meaning they were assured of a 2005/06 Champions League place.

As far as team news went, the main surprise from Liverpool’s perspective was the inclusion of Harry Kewell over French forward Djibril Cisse.


Cisse found himself on the bench, but Kewell only lasted 23 minutes of the tie before injury struck, Vladimir Smicer entering the field for what turned out to be his final Liverpool appearance.

Kewell, unfortunately, got to see his goalkeeper Jerzy Dudek pick the ball out of his own net, captain Maldini having volleyed home a Pirlo free kick in the opening minute of the encounter to hand Liverpool the worst possible start.

The Milan side were formidable, Maldini leading a defence which contained Cafu, Alessandro Nesta, and Jaap Stam.

Gattuso, Pirlo, Clarence Seedorf, and Kaka played in a narrow midfield diamond, with the imperious Crespo and Shevchenko up top.

It was the Brazilian Kaka that was tormenting Liverpool the most in the early stages.

And it was his slaloming run and dribble that cut open the Reds’ defence, just seconds after they themselves had a penalty claim turned down at the other end, that fed through Shevchenko.

The Ukrainian squared it to Crespo, who made no mistake at the back post.

Despite only 40 minutes having been played, 2-0 already looked like too tough a task to recover for Liverpool.

And it got worse for them just two minutes later, when Kaka turned provider and Crespo chipped it over Dudek to extend the scores to 3-0 going into half time.


Liverpool had started the final with a 4-1-4-1 formation, with Xabi Alonso sitting in behind Garcia, Steven Gerrard, Kewell and John Arne Riise.

But that was soon scrapped going into the second 45 minutes, a switch to 3-5-2 signalled when Dietmar Hamann replacing left back Steve Finnan.

That gave Gerrard more attacking freedom, being positioned as the sole attacking midfielder behind Milan Baros and Garcia.

The change immediately seemed to pay dividends for Liverpool, although Dudek was called into action early in the half to save a Shevchenko free kick.

You sensed that if Liverpool were going to haul themselves out of the wreckage, it would need a captain’s performance from Gerrard.

These were the sort of matches that Gerrard built a reputation on during his career, but that reputation had to start somewhere.

On 54 minutes, the Reds managed to pull one back.

Riise found himself in space on the left-hand side, before pinpointing a left-footed cross straight onto the head of Gerrard.

The Liverpool captain made no mistake, powering his header into the right corner.

Liverpool were now in the ascendency and had control over the ball in Milan’s half again just two minutes later.

Xabi Alonso worked the ball from the left to the feet of Hamann, who laid it off to Smicer.

The Bulgarian knew pre-match he was set to make his last appearance for Liverpool in Istanbul, Benitez having already decided not to renew his contract.

After a spell of injuries, he featured prominently in the 2004/05 season due to other injuries in the squad.

He said after the final that he was free in his head, that his motivation was to do well for the club in his last match.

And Smicer could have picked no better moment, firing home Liverpool’s second goal with a piledriver into the bottom left corner.

At 3-1, there was a small amount of hope brought back for Liverpool fans.

But now, just two minutes later, they firmly believed again.


Another four minutes had passed before right-back Jamie Carragher somehow found himself charging towards the Milan defence, quickly laying the ball off to Milan Baros in the 18-yard box before being tackled.

Baros held off two men before flicking the ball into a vacant area in the centre of the box.

In rushed Gerrard, unmarked and looking to be unstoppable.

Before he could reach the ball, however, Gattuso pulled him back – referee Manuel Mejuto Gonzalez had no choice but to point to the spot.

Xabi Alonso stepped up to the mark, looking incredibly to level the scores at 3-3.

His penalty, low down to Dida’s right, was expertly saved by the Brazilian, but there was to be no stopping Alonso as he threw himself at the rebound and fired the ball in.

Disbelief. Jubilation around half of the Olympic Stadium in Istanbul.

Liverpool had achieved the unthinkable in just six second-half minutes.

The game wasn’t over yet though – despite chances for both teams, the score remained deadlocked at 3-3 going into extra time.


The 30 minutes of extra time perhaps didn’t have the spark that the previous 90 had, but both sides were still well in the contest.

Shevchenko had his effort saved by Dudek before the rebound fell to the Ukrainian.

Dudek was the hero of the hour once again as he tipped his six-yard effort over the bar, but his night was just beginning.


Liverpool and Milan had both won their three previous European cup finals on penalties – one side would extend that statistic to four after the shootout.

Penalties are simple on paper – a one on one between the player taking the penalty and the opposing goalkeeper.

Penalties are not played on paper, of course, so Dudek and Dida, therefore, had a crucial role to play.

And Liverpool’s Polish shot-stopper gave the Reds an instant advantage, using a technique similar to Bruce Grobelaar’s ‘spaghetti legs’ in 1984 final.

Milan’s first taker, Serginho, fired his effort over the crossbar.

Dietmar Hamann volunteered to take Liverpool’s first, despite suffering from a broken toe.

He made no mistake, and Dudek sparked some initial celebrations as he dived low to save Pirlo’s effort.

Substitute Cisse, who hadn’t started the final, converted his spot-kick to give Liverpool a two-goal advantage after two penalties each.

Jon Dahl Tomasson finally got Milan on the board with his penalty, before Riise missed from the spot to give Milan hope.

Kaka, arguably the player of the first half, then made it 3-2.

Smicer then scored with his final touch in a Liverpool shirt to put all the pressure on Milan.

In other words, the all-conquering Shevchenko had to score or the game was over.

Jerzy Dudek stood tall in guarding the two goalposts that, remarkably, positioned themselves between Liverpool and the impossible.

After 45 minutes, they were 3-0 down.

How did Milan, world footballing giants, squander such a commanding lead?

Shevchenko, as players so often do in this scenario, fired the ball down the middle.

Dudek dived to his right but managed to stop the ball with his left hand to give Liverpool the glory they had been dreaming of.

Comeback well and truly complete.


The victory sparked large celebrations across Liverpool, with the final later dubbed ‘The Miracle of Istanbul’.

Milan were down but not out and redeemed themselves by winning the Champions League again in 2007.

Coincidentally, their opponents then were Liverpool, and despite a late Dirk Kuyt goal to halve the scoreline to 2-1, they could not repeat their 2005 heroics.

Jerzy Dudek made just six appearances for Liverpool the following season (none in the Champions League) after being replaced as number one goalkeeper by new signing Pepe Reina.

Man of the match Steven Gerrard scored 23 goals in all competitions the season after, guiding Liverpool to 82 points and 3rd in the Premier League.

The Reds finished top of a Champions League group that contained Chelsea, Real Betis, and Anderlecht but were knocked out in the last 16 by Benfica, 3-0 on aggregate.

Rafael Benitez stayed at Liverpool until 2010 when he left the club by “mutual consent”, having finished ninth in the Premier League the season before.

He then took up the vacant post at Milan’s rivals Inter a week later, replacing Real Madrid-bound Jose Mourinho.

After 2007, Liverpool would not contest the Champions League final again until 2018, but Jurgen Klopp’s side were defeated 3-1 by Real Madrid in Kiev.

They have, of course, followed that up with a second appearance in two years in the final, where they will take on Tottenham on June 2.