Having played out one of the most memorable Champions League matches of all time back in Istanbul in 2005, it seems incredible that Liverpool and AC Milan will meet outside of the final for the first time ever at Anfield in Group B on Wednesday.
But there was, of course, a second chapter to their shared history two years on from that dramatic Steven Gerrard-inspired comeback and Jerzy Dudek’s spectacular double save.
The two clubs headed to Athens for the 2007 final with very different motives. Milan wanted to get their revenge for the infamous Istanbul final two years earlier, while Liverpool were looking to equal the Italians as the second-most decorated club in European Cup history with a sixth win in the competition. The Italian giants had been inspired by the magic of Brazilian maestro Kaka in the semi-final as they bested Manchester United, with the midfielder scoring a brace at Old Trafford and inspiring a resounding 3-0 win at San Siro in a 5-3 aggregate success.
For Liverpool, it was history repeating itself as they outfoxed Jose Mourinho’s Chelsea once again in the semi-final. It took a penalty shoot-out for Rafa Benitez’s side to get by the Blues, with another familiar foe awaiting them in Athens.
Filippo Inzaghi made this final all about him, netting the first goal of the game just before the break when Andrea Pirlo’s free-kick deflected off the forward and escaped the already-committed Pepe Reina. The Italy international, who had long been haunted by Sir Alex Ferguson's claim that “that lad must have been born offside” in his critique of Inzaghi’s positioning in games.
He would double Milan's lead with eight minutes remaining, beating the offside trap and rounding Reina after an inch-perfect through-ball from Kaka. The Brazilian had run the show in midfield for much of the night, showcasing his claim to the Ballon d’Or which he would earn later that year. He would be the last winner prior to Luka Modric's 2018 win not to be called Cristiano Ronaldo or Lionel Messi.
Milan saw off any jitters remaining after their blown 3-0 lead of two years prior, even after Dirk Kurt had halved the deficit in the dying moments. Revenge was theirs, with Paolo Maldini lifting the club's seventh Champions League title. As for Benitez, his lack of clarity in the game led to some strange substitutions. In 2005 he had chanced upon all the answers, leading to a miraculous victory, but here he was short of resolutions when they were needed.
The defeat marked a tipping point for the Spaniard on Merseyside following those two European finals and an FA Cup win in 2006. By 2010, the Reds had become became the first of the Premier League’s well-established top four of Manchester United, Arsenal, Liverpool and Chelsea to drop out of the Champions League reckoning after an unbroken six-year spell. That failure to qualify for the 2010-11 edition would signal the end of Benitez’s spell in the Anfield hot seat.
In recent years, Liverpool have been able to experience some of those highs once more, recording a sixth Champions League triumph in 2019 and a 19th league title the following year. Milan, on the other hand, have had a torrid time in Europe since that final 14 years ago, with Wednesday’s game being their first in the Champions League since 2013-14. Such have been the relative experiences of the two clubs in recent years, Liverpool are huge favourites to get the result on Wednesday. Betfred are offering just 1/2 on a Reds victory, while Milan are out at 11/2.
There may well not be a repeat of the drama of 2005 when the sides collide once more at Anfield this week, but the final of 2007 was proof that there will always be something compelling about a clash between these two great giants of European football.