With contract negotiations between Milan’s senatori and the management set to be resolved tomorrow. Qasa Alom prepares himself for a new era at Via Turati, and looks back at some of the finer moments in the last decade.

“I hope this win can open up a whole new era for Milan. My own journey is almost at an end, but when a club invests in top players, it will win” Rino Gattuso May 2011.

Amidst Kevin Prince Boateng’s dazzling impression of Michael Jackson, Cassano being, well Cassano…the cheers, laughter and general jubiliation, Allegri being hoisted in the air by the whole squad and of course, Pato’s slightly awkward if not sincere moment with Ms Berlusconi one image stood out and resonated strongly with me from Milan’s recent Scudetto celebrations; an intense embrace between Clarence Seedorf and Massimo Ambrosini that seemed to last an eternity and betray a thousand emotions.

This was the first time football had left me with a tear in my eye since Roberto Baggio kicked a size five Adidas Questra into orbit back in the summer of 1994. Neither tears of sadness, nor tears of joy but rather tears of satisfaction, It had finally dawned upon me that soon there was to be a big Seedorf/Ambrosini/Pirlo shaped hole in my life and by Rino Gattuso’s own admonition this was finally the start of a new era.

There are five senior players whose contracts are all due to run out this summer, Alessandro Nesta, Massimo Ambrosini, Clarence Seedorf, Andrea Pirlo and Filippo Inzaghi. These stalwarts along with ‘Ringhio’ are the true spine of Carlo Ancelotti’s Byronic side that announced itself to the World at Old Trafford, sunk to an unfathomable nadir in Istanbul before gaining redemption in Athens . All of them are on the wrong side of 30, performing to their peaks much more sporadically and inevitably at least one of them will be preparing to put the famous red and black jersey on for the last time this coming Sunday and has stepped out to the Inno Ufficiale under adoration from the Curva Sud for the last time. So with all that in mind, let us take a brief moment to indulge on some of the players most memorable moments over the last decade.

10. AC Milan 2 – 1 Inter Milan, May 2008. Filippo Inzaghi.

It was hard to edge out that night in Athens, but the fact that I was part of the San Siro crowd that day makes this a special memory for me. Over the years “Superpippo” has etched his name into Milanese hearts with countless last gasp winners, constant bickering with the linesman and then moments of pure uncontrollable joy. This match encapsulated what Filippo Inzaghi is in 90 minutes. With Milan needing to win to maintain their Champions league hopes as well as stop Inter from winning the title in the derby, the Rossoneri simply had to win. In the first half, Excellent movement followed by countless misses led the crowd to vilify SuperPippo at half-time, however early in the second half a darting header to set Milan on their way to victory made everyone forget the hatful of chances he missed. Typically after these heroics Milan lost pathetically the following matchday to end up settling for the Uefa Cup. That was simply how Milan rolled…

9. Manchester United 3 – 2 AC Milan, February 2007. Massimo Ambrosini

Though Kaká and Seedorf stole the show, it was Massimo Ambrosini who provided the missing link and gave the team the balance that year. Although the side lost at Old Trafford, Ambrosini was excellent throughout going about his janitor role quietly and effectively, to hint at the captain he would become a couple of seasons later.

8. Manchester United 0 – 1 AC Milan, February 2005. Clarence Seedorf

A tight affair that was decided in both legs by a single goal – much was made before the tie about the threat of Rooney and Ronaldo, or Crespo and Kaká, but in the first leg at least Clarence Seedorf was at his powerful best. Running hard all over the place, marking, tackling and then providing the link to the front 3, Seedorf proved that he was the teams big match player and was thus marked out by Sir Alex Ferguson as the man he feared the most.

7. Ajax Amsterdam 2 – 3 AC Milan, April 2003. Filippo Inzaghi

Trailing 2-1 with only half an hour to go, it’s hard to imagine what the sides trajectory would have been like, had Milan been dumped out in the quarter finals of the Champions League that year. Thankfully, Inzaghi was excellent all season, the hunger and desire was plastered all over his leathery face and he fought with every sinew in his body to will the side into the Semi’s. I still don’t know how Filippo managed to looped over the cross for Shevchenko to head home the equalizer, but as soon as that happened, I knew he would find a last minute winner from somewhere.

6. Milan 3 - 1 Parma, March 2002. Andrea Pirlo

Back before Andrea Pirlo was “Andrea Pirlo” he was a troubled teen with phenomenal technical ability but no defined position. Successive managers wouldn’t know where to play him but merely bring him on for the last 20 minutes or so. And whilst Pirlo was arguably the crown jewel in Carlo Ancelotti’s midfield diamond, the player that redefined the holding role, it was before then that il Maestro perhaps gave his most telling contribution to the cause. In the 2001/2002 season Milan were struggling in the league, and Bologna looked certain to grab fourth spot. However a criminally underappreciated Pirlo started to become more than a bit player, and in short sharp bursts grabbed Milan by the scruff of their necks and was the biggest factor in getting them into the champions league for 2003. His set pieces in particular were a  huge threat, just like in this game against Parma where he fooled everyone by going the other way around the wall.

5. Reggina 0 – 1 AC Milan, January 2008. Alessandro Nesta

It’s hard to pick out one moment for a man who’s had such a consistently good career, however in this game Nesta was simply playing another sport. The likes of Kaká and Gilardino were toiling away in the rain on the other side and the whole team was pressing forward searching for that goal, fully in the knowledge that a rejuvenated Nesta was behind them. The former Lazio captain seemed to have a telepathic ability, and stopped any attacks from even before the opponents thought about them, and of course that one lasting image, the way he slides along the ground, tackles and then gets up in one clean movement before passing the ball on, and casually flicking his hair.

4. PSV Eindhoven 3 – 1 AC Milan, May 2005. Massimo Ambrosini

Another last gasp goal, another dramatic finale. Milan had no right to get to Istanbul that season, as PSV were the better side, but in injury time, Ambrosini leaped highest and headed past Gomes. It must have been frustrating for Max at the time, behind Gattuso in the pecking order, he often found himself on the bench, but his aerial ability and red faced dedication left him with the unerring ability to be a true clutch player.

3. Milan 2 – 2 Chievo, March 2004. Andrea Pirlo

Again finding themselves 2-0 down at half time, Milan threw on Shevchenko to change things. Yet it was Pirlo who provided to be the difference. A gorgeous ball over the top for Shevchenko’s goal to bring it back to 2-1, followed by a magnificent out swinging smack to tie the match. The sort of Pirlo wonder-goal that became an infuriating annual tradition; whether against Cagliari the following season, or more recently like the strike last season against Real Madrid or this season against Parma, these goals would make you sit up and behold his striking ability, and then lament him only doing it once or twice a season!

2. AC Milan 4 - 1 Bayern Munich, March 2006. Filippo Inzaghi

A defensive mix up and a sprawled Oliver Kahn leave Filippo with the simplest of tap ins from half a yard out, yet his first attempt goes backwards. Nonetheless Pippo flaps around like a fish out of water and heads the ball like a seal just over the line. That single moment provides everything you need to know about the Milan number 9, horrible technique and no grace about his play whatsoever, despite all that he will find a way to put that ball in the back of the net, and then celebrate like it was his first goal.

1. AC Milan 3 – 2 Inter Milan, February 2004. Clarence Seedorf

Inter stormed to a commanding 2-0 lead at half time and Adriano in particular was in ominous form. The second half turnaround though was the stuff of legends and continued the sides’ reputation as comeback Kings. Kaká and Tomasson drew the game level, then with less than five minutes left on the clock and out of nowhere, Seedorf drifted infield from the left, fired a rocket into the left corner and caused Carlo Ancelotti to go absolutely mental on the sidelines.

After all that gushing nostalgia, it’s hard to imagine a Milan team without these players in the side however under Max Allegri and the managements’ guidance the players have already begun to be replaced. A common pattern that is evident from these memories has been each players ability to stand with broad shoulders and define a match. Each player had that characteristic of being a big game player, therefore it was difficult for opponents to simply target one danger man. In the current crop, we’ve already witnessed the ability to grinding out wins against provincial sides, however there are serious doubts over the players capabilities at taking responsibility on the biggest occasion. The management’s biggest challenge will not be replacing the individual talents of the Senatori but finding a new generation with the magical glint in their eyes for the spectacular that proved to be the hallmark of this generation’s Romantic, frustrating and relentlessly dramatic side.