Can Ancelotti see off City to enter history books again?

After becoming the first coach in history to win all five of Europe's top-five leagues, Carlo Ancelotti can enter the record books again if his Real Madrid side can see off Man City.

Real's 4-0 win over Espanyol on Saturday put him alone in managerial history in leading teams from Serie A, the Premier League, Ligue 1, the Bundesliga and La Liga to league titles.

The 62-year-old is already the first man to lead four different clubs to the Champions League semi-finals, and with his side trailing Manchester City 4-3 from the first leg at the Etihad Stadium, needs only a slight change in fortunes to reach the final - which would make him the first manager to do so five times.

He was victorious in his first Champions League final with a penalty shoot-out win over Juventus at Old Trafford in 2003, but two years later was beaten on spot kicks after a stunning comeback from Liverpool in Turkey. Another two years on and he got his revenge, as Milan beat the Reds 2-1 in Athens.

Despite his close and long-term relationship with the city of Milan, perhaps his best final was saved for his first spell at the Bernabeu, where he finally helped Real Madrid to 'La Decima', their 10th Champions League trophy, an achievement they had waited 12 years to realise.

Eight years on from last lifting the European Cup, Wednesday's game in Madrid offers him the opportunity to move within 90 minutes of adding a fifth winners' medal to his collection - which would earn him another record in itself.

It marks an impressive first season back in the Spanish capital, which had started with a certain degree of apathy towards his return.

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Spanish football journalist Tom Allnutt told Sky