Truth be told, prior to the 90s, there really was not any kind of bond between the two clubs, with the last time the Rossoneri visiting Ibrox being on the 27th of November 1957 in the-then European Cup where the Italian giants triumphed to the tune of 4-1. The return leg on the 11th December was another victory for Milan, 2-0. They went onto the final, only to be edged out after extra time by Di Stefano’s mighty Real Madrid.

Indeed, the fledgling relationship did not really start tenuously until 1993, when Rangers excelled so astonishingly in the inaugural Champions League. Missing out on the final by a single match, their conquerors Marseille went onto beat Milan in the final, but the domestic match-fixing scandal which saw club supremo Bernard Tapie eventually jailed engulfed the French side in the months following their triumph. It remains a bug-bear to many Rangers fans who consider themselves cheated out of a Champions League final place, and indeed many proposed a ‘rematch’ between the losing finalists Milan and Rangers. Sadly, of course, this never took place.

One year later, in July 1994, the relationship grew a little further when one of the greatest Rangers of all time, and the idol of yours truly, Brian Laudrup, made the switch from the San Siro to Ibrox, belatedly following his country’s sensational victory at the 1992 European Championships. This was a tournament where Denmark had replaced the politically omitted Yugoslavia, as rank outsiders, and one which truly brought Brian to world prominence. So it was a outstanding coup for Walter Smith to bring the player from Italy, where, frankly, his career had stalled. He went on, of course, to have a quite sterling career in Govan.

There would be no point in discussing any relationship between the clubs any further without exploring one of the biggest links between the two, one which started indirectly 3 years later. This was, of course, the low-key signing by Rangers of one Italian youth player, Gennaro ‘Rino’ Gattuso from Perugia. He joined alongside Marco Negri, also from Perugia, who went on to have a stunning first half of his debut season with 32 goals, before bizarrely disappearing from the first team with a reported ‘eye’ injury. Gattuso had a productive time at Ibrox, becoming close with manager Walter Smith, before his time soured under new manager Dick Advocaat when he was played out of position and his relationship with the Little General faltered. I had the pleasure of meeting both players during a signing session where they promoted Italian football boot brand ‘Pantofola d’oro’ – Negri was charming and charismatic, while Gattuso sat alongside him, timidly, shy, and very quiet. How things have changed…

As we know, Gattuso moved onto Serie A side Salernitana a year later in October 1998 for a very healthy £3.5M before switching to the Rossoneri for a reported 8M Euros a year later again, with suggestions at the time that a sell-on clause would net the Ibrox club £1M further. This was never verified officially but it was at this point that a real friendship between the clubs began to tentatively emerge, given Gattuso remained in very tight cohorts with former manager Walter Smith, who he continued to view as a psuedo-father figure, speaking regularly. Indeed, when he was linked to Chelsea in 2009, Gattuso said the following about the influence of Smith:

            “He was the best man for my career, because I was a young player and it was a big chance for me to play at a big club. Sometimes I speak on the telephone to the gaffer. He’s a nice person for my job and the same for my life.”

Gattuso is married to a Glaswegian girl who he met in Canada, and speculation has linked him doggedly with a return to Govan. Smith himself of course returned to the Ibrox hot seat in 2007, so that speculation intensified.

With Gattuso on board at Milan, a friendly, quite possibly inspired by Gattuso’s continuing relationship with Rangers, Smith and Scotland, was arranged for 2002, Sunday July 30th at Ibrox against the Italian giants. An afternoon kick-off in front of a very respectable 40k+ crowd saw a pleasing 2-2 draw, with goals from de Boer and Caniggia for the home side, and Tomasson and Borriello for the visitors.

The clubs’ friendship became almost categorically established 7 years later when another friendly was arranged for 5th February 2009, again at Ibrox, and this time the attendance topped 45k. For a friendly match this was quite extraordinary, most possibly helped by ‘Beckham Mania’, due to the English midfielder’s loan spell at the San Siro from current team LA Galaxy. Astonishingly this friendly too ended 2-2, with one especially nice moment where Milan superstar and Brazilian ‘trequartista’ legend Kaka scored an exceptional solo goal and applause greeted it from every inch of the stadium, to which the Samba star reciprocated his own praise of the watching audience. David Beckham’s involvement lasted just the first 45 minutes, but the global phenomenon that he is, this was enough to satisfy those who desperately wanted a glimpse of him. Undeniably, this involved quite a few bearettes…

The latest chapter in the clubs’ bond is of course the upcoming charity match between legends from both teams – Rangers Legends V AC Milan Glorie. Arranged last year, the purpose of this match (and an accompanying dinner) was to raise funds for charities from each. Sadly, due to Rangers’ off-pitch financial difficulties, the Charity Foundation has had to suffer a hit to its cut, which will go into the club itself instead, but in the name of keeping Rangers afloat, it is a necessary evil.

The match will feature a glut of incredible names from both clubs’ recent history, with Giovanni Van Bronckhorst the latest confirmed name to line up for the light blues. Previously-announced legends starring for the home side include Richard Gough as captain, with Brian Laudrup (who of course will be facing his former club), Ally McCoist, Mark Hateley, Paul Gascoigne, Andy Goram, Lorenzo Amoruso, Jorg Albertz, Michael Mols, Trevor Steven and Arthur Numan. Walter Smith will manage.

The visiting Rossoneri’s roster is mouth-watering in its own right with the likes of Franco Baresi captaining, and Paolo Maldini, Frank Rijkaard, Jean-Pierre Papin, Alessandro Costacurta, Christian Panucci, Gianluigi Lentini and Zvonimir Boban starring. The only missing player I would personally have loved to turn out for the visitors is Ruud Gullit.

Unfortunately the ticket uptake for this match has not been as swift as had been hoped, with latest reports estimating around 35000 seats have not been sold. With 9 days to go and exceptionally modest prices for both adults and children, hopes are optimistic that there can be a stark upturn in ticket sales in the days leading up to the match.

To order tickets and boost the attendance, visit the official sales site.

However, red and black scarves, the colours of Milan, have been on sale from Rangers in the last week to raise funds in this time of financial peril, and have been selling very well indeed – while this is not directly an intentional homage to the men from Italy, it does refer to the old Rangers Swifts, whose kit was very similar to the historic vertical red and black stripes of the Rossoneri.

These scarves can be ordered here.

The match a week on Friday promises to be a truly nostalgic trip down memory lane for supporters of both sides, and indeed neutrals who simply love the game. The calibre of player booked for the game is inspirational, and while the crowd is unlikely to witness a blood and thunder encounter, the chance to see some of the greatest players from either club is a truly momentous occasion and a further example of the continuing bond between both clubs.

Possibly in the future some link could be made, when Rangers are in a better position, where the club gets first refusal on some of AC’s more promising youth talent from their youth team the ‘Primavera’. With some of the home-grown players Milan have recently produced, such Antonini, Abate and arguably, going back in history, Ambrosini (signed at the tender age of 18 from Cesena in 1995), there is a pool of talent at Milanello which, arguably, could benefit from experience in the SPL at Ibrox. After all, it did Gattuso no harm. But this is hypothetical and Rangers have more important worries to contend with for now.

That said, it is personally a marvellous concept for me to witness a bond forged between both clubs. As a supporter of both it gives me a great deal of pleasure to see both great clubs sharing so much in the last 20 years, and I can only hope it continues.