Padraig Whelan Date: 22nd October 2020 at 11:30am
Written by:

AC Milan travel to Scotland on Thursday night as they kickstart their Europa League group stage game with a trip to Glasgow, where Celtic await.

They have been relatively familiar foes, particularly over the course of the last two decades.

We take a look back at their memorable meetings from down the years.

European Cup quarter-final 1968/69

The first ever showdown between the pair came over 50 years ago, when both were among the most feared sides on the continent.

Celtic were just two years removed from vanquishing their opponents’ city rivals Inter to lift the European Cup for the first time, while the Rossoneri had also achieved that feat in 1963.

A violent snow storm in Milan threatened the first leg of their quarter-final in February 1969 but after 200 workers tirelessly removed up to five inches from the field, the game went ahead, although the visitors lodged a complaint as they felt visibility was so poor that the game should have been postponed.

Unsurprisingly, given the difficulty of the conditions, neither side managed to muster much and the game ended in a scoreless draw ahead of the return leg in Scotland.

There, an early goal from Pierino Prati in capitalising on a defensive mistake proved the difference and negated the need for a third play-off tie in Belgium.

Milan went on to win the competition, overcoming Manchester United in the semi-final before easing past Ajax to lift the trophy for the second time.

Champions League group stage 2004/05

It was 35 years before the Scottish and Italian giants were pitted together again, in a tough Champions League group which also included Barcelona and Shakhtar Donetsk.

Their first meeting again came in Italy, where a daunting prospect awaited the travelling side against a Milan outfit who were in the midst of another golden period, particularly when it came to the continental stage.

Kaka, who would go on to torture the Hoops again in future, weaved a perfect pass through for Andriy Shevchenko to give them an early lead but a bullet header from Stan Varga in the second half looked like rescuing an impressive point.

However, a combination of both Celtic’s unwavering inability to shoot themselves in the foot away from home in Europe and Milan’s never say die attitude saw Filippo Inzaghi and Andrea Pirlo strike with two goals in the final two minutes to salvage the win.

The second leg in Glasgow was a much tamer affair, with Milan already through by the time they met on matchday six. A Serginho strike which hit the bar was as close as either side came in a game in which the home side shot away from the traditional ‘Celtic End’ for the second half, a rarity at Parkhead.

What happened next for the Rossoneri in the competition is something few want to be reminded of. They reached the final in Istanbul against Liverpool, where they were defeated.

Champions League last 16 2006/07

When the sides met in the first knockout round of the Champions League in Glasgow’s East End in 2007, it was a special occasion – being the Bhoys’ first ever game at this stage under the modern format, while also being the legendary Paolo Maldini’s 100th game in the competition.

He and his teammates defended well in front of a boisterous home support and had the better chances, with Alberto Gilardino denied by a fantastic feet stop and former Rangers man Gennaro Gattuso narrowly missing out on a goal he would have craved.

That left it all to play for ahead of the return leg at San Siro, where again Carlo Ancelotti’s men created more but were met with more inspired goalkeeping from future Fiorentina star Artur Boruc.

Celtic should have been given a penalty for a Maldini handball but were largely lacklustre in attack, with their strong defending sending the tie to extra-time after 180 scoreless minutes.

And it was there that an early goal from European Footballer of the Year, Kaka, settled it as he glided forward unchallenged from the halfway line and squeezed the ball home.

For the third time in succession after playing their lucky omens Celtic in this competition, Milan reached the final, where they gained revenge on Liverpool thanks to Super Pippo’s heroics in Athens.

Champions League group stage 2007/08

Just seven months after their agonising loss at San Siro, fate delivered the Bhoys with the perfect opportunity for some vengeance of their own when they were grouped with the holders in the following season’s competition.

And they made the most of it, Yoann Gourcuff being unable to clear a Stephen McManus attempt off the line as Celtic took a second half lead only for their old nemesis Kaka to stroke home a penalty shortly afterwards to level.

Incredibly, that strike from the Brazilian was the first ever penalty scored by an opposition player at Parkhead in a European game (excluding shootouts), per the reliable Celtic Wiki.

Undeterred, Celtic rallied to win it at the death thanks to Scott McDonald’s close range finish, although the game is also infamous for two other memorable incidents.

Following that goal, an over-exuberant home fan ran onto the field to celebrate and made minimal contact with goalkeeper Dida, who was stretchered off feigning injury, having first attempted to chase his ‘assailant’.

It was also the night when Gilardino attempted one of the worst dives ever seen on a football pitch, for which he was booked. If you haven’t seen it, seek it out.

The return fixture saw Milan quickly regain the upper hand as Inzaghi’s record-breaking second half goal was enough for a Milan win, with that strike making him the then leading scorer in UEFA competitions.

Both teams still made it out of the group, although neither went any further than the last 16 – Milan losing 2-0 on aggregate to Arsenal, while Celtic were beaten 4-2 by Barcelona.

Champions League group stage 2013/14

The most recent meetings between these clubs were both dominated by the Rossoneri in the group stages of the Champions League seven years ago.

San Siro once more played host to the first fixture, where Anthony Stokes crashed a free-kick against the crossbar for the visitors, who were again undone by a mixture of misfortune and disastrous defending.

Neil Lennon, who is in charge at Parkhead again after returning for a second spell, watched his side hold out for 82 minutes before Emilio Izaguirre deflected a wayward Cristian Zapata strike into his own net.

A Mario Balotelli free-kick was then saved brilliantly by Fraser Forster, who was helpless to prevent Sulley Muntari (who had earlier missed a sitter) from bundling the ball home.

The second meeting in November on a cold, rainy Glasgow night was far more convincing in favour of the Rossoneri, who ruthlessly put their hosts to the sword.

Yet again, it was that man Kaka who proved a thorn in their side when, back for his second time of it at the club, he was afforded the freedom of the penalty area to nod in the easiest of headers, a rarity for the former Real Madrid man.

After Virgil van Dijk missed a tantalisingly easy chance to level, Milan pounced and Zapata and Balotelli both notched the goals they were denied in the previous meeting for a comfortable 3-0 win.

Unfortunately for the Diavolo, they were dispatched with ease at the last 16 phase by Atletico Madrid and have never featured in the competition since.