5. Hernan Crespo - Chelsea to AC Milan (season-long loan, 15th July 2004)
Hernan Crespo was a fast, tenacious striker who possessed good technique and could score goals with both feet and was exceptional in the air. A prolific and opportunistic goal-scorer, he was known for his ability to score acrobatic goals.
In 2004, newly appointed Chelsea manager Jose Mourinho deemed Hernan Crespo surplus to his requirements following the arrival of Didier Drogba and allowed him to be loaned to Italian giants AC Milan. He returned to the Serie A, where he had spent 7 successful seasons after just one year at Chelsea. His transfer to Lazio from Parma in the year 2000 had been a world record transfer at £35 million involving cash payment of £16 million and player sales of worth £19 million.
Crespo scored 10 goals in the league and twice in the Champions League final defeat against Liverpool in Istanbul, before returning to Chelsea in 2005 winning the Premier League in the 2005-06 season. He then left for Inter Milan in 2006, initially on a 2-year loan deal and then permanently on a free transfer in 2008, winning the Serie A in each of his three seasons in his second spell with the club. He then moved to Genoa and winded his career down at Parma.