Tottenham prepare to take on i Rossoneri tonight - but who would win if the two clubs' greatest ever players were assembled for the mother of all European ties?
GK – Ray Clemence
The curtain was coming down Ray’s career around the same time I realised that professional football was not like school where goalkeepers were chosen because they were the worst on pitch. When I think of Tony Parks, Erik the Viking, Walker, Robbo, Gomes et al I’ve got clear memories of them throwing one in over their shoulder at some point. All I remember about Clemo was that he had massive hands. 8
RB – Steven Carr
Like a milky Roberto Carlos, Carr saved, made and scored goals. He was our best player for a period in the late 90s and was gearing up for the inevitable exodus to Man U until he suffered a knacked knee in 2001. Was never the same player after that and went on to be shit for Newcastle, which was nice. 8
CB – Ledley King
For ten years I’ve been trying to instigate a chant to the tune of 10cc’s ‘Dreadlock Holiday’ that goes ‘I don’t like Ledley, oh no, I LOVE HIM’. For some reason it hasn’t caught on but that doesn’t make it any less true. If knee transplants were available at the beginning of the century Deadly Ledley would have 50 England caps and we would’ve lost him to a European giant. In reality having Ledley at the back has convinced Spurs fans you can stick Sol Campbell up your arse, which can’t be easy. 10
CB – Graham Roberts (C)
If I’d made this list on July 1st, 2001 it would be big Sulzeer partnering Deadly. But I didn’t and that’s why Roberts gets the nod. A man made of granite with an iron will, Roberts lead by example during our most successful period of my lifetime. He played like a fan in a Spurs shirt and was a fucking nutcase. What’s not to like? 9
LB – Gareth Bale
Probably not the best left back I’ve seen at the Lane but with the quartet of greats ahead of him in midfield it’s the only way the Welsh wizard would get in the side. Another forward thinking player in this attack minded dream team adopting the rarely used 1-0-10 formation. 8
RW – David Ginola
With Gallic flair and that head of hair David was born to play for Spurs. During the dark days of the late 90s when a decent cup run and good performance against Ars*nal is all most Spurs fans wanted out of a season (and still never got) Ginola was a rare beacon of hope. It was a horrible time, with double agent Graham in the dug out serving up turgid, functional football. Ginola’s flamboyant style off the pitch and PFA player of the year performances on it were our only connection to our ‘Glory Glory’ past. 9
CM – Paul Gascoigne
In April 1991, on a sunny afternoon in Wembley, Gazza made Barry Davis say, “Is Gascoigne going to have a crack? He is you know. Oh I say that is…schoolboys own stuff” as he smashed in the best free kick the old stadium had ever seen past David Seaman. He obviously did loads of other stuff that makes him worthy of a place but the joy I felt after that swing of his right foot is more than enough. 10
CM – Glenn Hoddle
A magician who was more dexterous with his feet than most people are with their hands, Hod Almighty is the reason I support Spurs. Bags of skill, flair to burn and an eye for the spectacular; Glenn was the archetypical ‘Spurs player’. Put simply he’s the most naturally gifted Englishman to play in colour. Despite looking like a lesbian Desperate Dan and coercing Waddle to do Diamond Lights, Hoddle will forever be the ‘King of White Hart Lane’. 10
LW – Chris Waddle
Revered by Marseille fans as much those at Spurs, the Waddler is an absolute hero. The enduring memory of the lad who used to work in a sausage factory in Gateshead is of him always looking knackered, marauding down the wing, dropping his shoulder and ghosting past defenders with his magnificent mulleted mane billowing in the breeze. If Aslan improved his touch, put on a Geordie accent and donned a Hummell shirt he still wouldn’t look as majestic as Chris in his pomp. 9
CF – Gary Lineker
There’s a generation who only know Gary as the jug eared crisp thief who ruined the golf. Yeah? Well they can fuck off because Lineker was a goal poacher without equal. A great ambassador for us who always did the biz in the big games, Lineker consistently reproduced his England exploits in the lilywhite shirt of Tottenham. 10
CF – Jurgen Klinsmann
This was a tough one between Jurgen and Teddy Sheringham. Both had two stints at the club, played with the first three yards in their head and lit up the Lane. Teddy played more than one and a half seasons for us, but Klinsmann invented the diving celebration, which gets my vote. Part of the first wave of genuine world superstars to join the Premiership as it was then known, Jurgen had me believing that the mid 90s were the beginning of a Spurs renaissance. It wasn’t. The most decorated footballer in my team. Also drove a Beetle. 9
Manager – Osvaldo Ardiles
Keith Burkinshaw, Terry Venables and Harry Redknapp might have something to say about it but with this team packed with attacking talent there’s only one kamikaze manager I’d want to take the reins. I met Ossie once – he was an absolute gent and even got the coffees in – and he said of his time at Spurs “I knew exactly how Tottenham wanted to play and it was the way I wanted to play.” It’s the way I’d want this team to play as well. It looks like me and Ossie share the same dream. 6
GK- Fabio Cudicini
The father of Tottenham shot-stopper Carlo helped Milan win their second European Cup in 1969, and their first Intercontinental Cup the same year. He also won a Scudetto, Cup Winners Cup and Coppa Italia in his 183 games for the club. 7.
RB- Marcos Evangelista de Morais (Cafu)
Nicknamed the ‘pendolino’ for the speed and power at which he blitzed down the flanks. He arrived at Milan a World Cup winner twice with Brazil 1994 and 2002, and he won the Champions League with the Rossoneri in 2007 against Liverpool in Athens, as well as the FIFA World Cup that year. 8.
CB- Alessandro Costacurta
Alongside Franco Baresi, Costacurta is arguably Milan’s greatest ever centre-back. He won five European Cups, seven Scudetti, two Intercontinental Cups and a hoard of other trophies in a 20-year career at San Siro. 10.
CB- Franco Baresi
Milan retired the number six jersey when Baresi hang up his boots in October 1997 after two decades at the club. A legend in his own right and one of the greatest defenders the world has seen. He captained the team to great success including three European Cups, two Intercontinental Cups, six Scudetti, three European SuperCups and many others. 10.
LB- Paolo Maldini
Perhaps the greatest defender of all time in the history of world football – the model footballer in every sense. 26 trophies in 25 years at Milanello says it all, among those were five European Cups and as many Intercontinental Cups as well as seven Scudetti. 10.
RM- Dejan Savicevic
The Montenegrin winger will best be remembered for his stunning lob over Barcelona goalkeeper Andoni Zubizaretta in the 1994 Champions League final as Milan bashed the favourites 4-0 in Athens. A classy midfielder who also won three Italian titles and a European SuperCup. 7.
CM- Gianni Rivera
Played under the legendary coach Nereo Rocco and alongside Giovanni Trapattoni to help Milan win their first European Cup at Wembley in 1963 against Eusebio’s Benfica. He repeated the feat in 1969 with another European Cup. He became the first Italian to win the Ballon D’Or whilst playing for the Rossoneri. 8.
CM- Frank Rijkaard
A versatile midfielder who played alongside Ruud Gullit and Marco Van Basten, Rijkaard was part of the team who won back-to-back European Cups in 1989 and 1990 when he scored the only goal of the game against Benfica. 9.
The world stood up and took note of Kaka when his three goals against Manchester United over both legs of the 2007 semi-final saw Cristiano Ronaldo live in the shadows. Kaka was Milan’s passport to the Athens final where he helped his team exact revenge over Liverpool for the heartbreak of Istanbul two years earlier. He also won the FIFA Club World Cup. That stellar season rewarded him with both the Ballon D’Or and FIFA World Player of the Year awards – simply sensational. 9
CF- Ruud Gullit
The Dutchman had it all when he arrived at Milan for the 1987/88 season as the world’s most expensive player and Ballon D’or Winner. He proved his worth on the pitch with force and effect and scored twice in the 1989 European Cup final in a 4-0 win over Steaua Bucharest. Won it again the following year. 9.
ST- Marco Van Basten
One of the greatest strikers of all time and the most complete. Van Basten had everything in his locker and his quality helped Milan conquer the European Cup three times. He also won two Intercontinental Cups and four Serie A titles among other trophies. Three Ballon D’Or’s during his time at San Siro pay homage to a true great. Sadly his high-profile career was curtailed by an ankle injury which forced his retirement at just 30 in 1995. 10.
Manager- Carlo Ancelotti
Nils Liedholm, Fabio Capello, Nereo Rocco and Arrigo Sacchi could have made this list, but Ancelotti is, perhaps, Milan’s best-ever coach. He won 17 trophies as a player and manager at the club. As a coach he won the Champions League twice in 2003 and 2007 having already conquered the European Cup as a player in 1989, and then 1990. Led Milan to the 2007 Club World Cup. Delivered the Scudetto in 2004 after a five-year drought. 9.
Total Score: 107
Milan shade it by a single point. Despite an entertaining performance by Spurs with Gazza and Hoddle sparkling in midfield, the Italians snatched victory through two late strikes by Van Basten and Kaka. A sickener.
Tottenham 3: Bale (2) Gascoigne (16) Klinsmann (89)
Milan 4: Van Basten (5, 90) Gullit (35) Kaka (90+1)
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