Date: 5th May 2015 at 8:00am
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Carletto may be one of the most illustrious coaches in history, but his time at Juve is surely a coffee stain on the rich fabric of his career.

“Yes, I did raise my middle finger, and it was my response to ignorant people,” said then-AC Milan coach Carlo Ancelotti.

This incident, which saw him make an inappropriate gesture towards some Juventus fans in the pre-season Trofeo TIM game back in 2008, was the result of having been the target of abuse from the home team’s supporters.

In May 2014, the Italian became only the second coach to win the Champions League thrice, confounding the odds on betfair; but not everything was fun and games for the former midfielder, having endured a troublesome spell as coach of the Bianconeri between 1999 and 2001.

ancelotti

On Tuesday, Ancelotti once again returns to Turin, this time to face Juventus in the semi-final of the Champions League and as coach of Real Madrid.

When Ancelotti was appointed as coach of Juventus in 1999, fans were livid, not because of his record as a coach but because the former’s playing career comprised of successful spells at rivals Roma and AC Milan.

Not only that, but Ancelotti contested a fierce title race with the Bianconeri as coach of Parma in the 1996-97 season, finishing only two points behind Juve. He was considered an ‘enemy’. He was loathed.

Some Juventus fans even went as far as putting up a banner reading “A pig can’t coach” following Carletto’s appointment, as a dig at his physical appearance and his roots, since he hails from the famous ham-processing area Emilia-Romagna.

Despite early criticism though, Ancelotti was able to win the now defunct Intertoto Cup at the start of the season by defeating French outfit Rennes 4-2; but things went downhill from there.

In 1999-2000, Ancelotti’s Juventus endured a very difficult title race with Lazio. Despite the fierce competition early on in the season, the Bianconeri went nine points clear at the top with eight games remaining — but after a series of slip-ups, the difference was reduced to only two points heading into the final game of the season. Lazio were due to host Reggina, whilst Juventus travelled to face Perugia at the Stadio Renato Curi.

ancelotti perugia

Lazio did their part by beating Reggina 3-0, but were waiting for Juventus’ game to finish, which was temporarily abandoned due to a waterlogged pitch.

Ancelotti’s men set out on the field knowing that a win would crown them Serie A champions — but it simply wasn’t meant to be. Alessandro Calori scored to gift the Grifoni a win. Lazio were champions.

Another heartbreak soon followed. This time the Bianconeri lost out on the Scudetto to the other Rome club, Roma in the following season — finishing two points off first place. Ancelotti’s men had the chance to go top of the table when they faced Roma in May 2001 however, only five games before the end of the season, but once again the tables turned against them.

Goals from Alessandro Del Piero and Zinedine Zidane gave the Bianconeri a 2-0 lead in the first six minutes, but Fabio Capello’s men scored twice in quick succession via Hidetoshi Nakata and Vincenzo Montella to remain top.

Montella

That season proved to be Ancelotti’s last at the club, with his sacking announced at half time in the final day of the season against Atalanta, despite Juventus being mathematically in the title race.

Recalling his time at Juve in his autobiography titled “My Christmas Tree”, Ancelotti revealed that he felt lonely at the club, pointing out that the club management were only worried about French star Zinedine Zidane.

“I started to feel lonely, because whenever [former club president Giovanni] Agnelli came to the locker room he would say hello to [Alessandro] Del Piero and go to Zidane. The same with [Luciano] Moggi and [Antonio Giraudo], it happened dozens of times. Everyone ignored me, they went there to see Zidane.”

“Juve were too glamorous for my liking, they were the posh kids; we were different. I was a country boy, they were executives in suits. Swatch against Rolex. Plastic against Gold.

“Juve was a love story that never began.”

Carletto got his revenge only two seasons later, this time as coach of AC Milan, when he won the Champions League against Juventus, thus denying them a third triumph.

“It was incredible to see the entire Juventus end of the stands motionless. It looked like a poster. I wanted to take it off the wall and carry it home with me,” Ancelotti recalled.

ancelotti milan

Tuesday’s semi-final is a game with great magnitude; but even though all eyes will be on the potency of Crisitano Ronaldo and the tranquility of Andrea Pirlo, the rivalry between Ancelotti and Juventus gives it an overwhelmingly unique taste.