A much-travelled player for one so young, Maccarone started off his career with Italian giants AC Milan in their youth programme. He then had a spell with Modena, but it wasn't until he signed for Prato in January 1999 that he finally got a taste of first team football. After Prato he switched to Varese, before returning to Prato - where he finally began to play the football he is clearly capable of. The bigger clubs then began to show an interest in the forward again and in the summer of 2000 he moved to Empoli.

Maccarone soon settled into the Empoli first team, and before long was an established member of the Italian Under-21 squad. He was showing rapid progress at the Serie A club, and eventually won his first full cap against England in March 2002, earning an injury-time penalty that set up up a 2-1 win for his side. The 2002 World Cup came just too quickly for him, but he was expected to be in the shake-up once the 2004 European Championships in Portugal came around.

By the end of the 2001/02 season, the world and its mother had been linked with the exciting player. His reputation was enhanced by some great displays in the European Under-21 Championships in Switzerland. He scored a superb goal... against England. No wonder, then, that he fancied a move to the Premiership after causing the cream of English defenders so much trouble. And so it was, in July 2002, that he chose Middlesbrough ahead of all his other suitors and joined the club for £8.15million.

Boro boss Steve McClaren told the club's official website: 'I saw him early on for the Under-21s and we checked him again in the Championships. He did well and we've done our homework on him, he has great potential, has done ever so well and we're pleased to be able to sign a player of that quality for Middlesbrough. The striker made his Boro debut in a goalless draw at Southampton, and in his next game bagged a brace in a 2-2 draw at home to Fulham. After netting four times in his first eight appearances, Maccarone began to struggle with the English game. Although a tally of nine goals was far from poor, many had expected better for the fee paid.

McClaren was insistent that Maccarone would come good in the 2003/04 campaign after bedding into the Premiership, but he missed the first two months of the season after suffering an ankle injury in a pre-season friendly at Hull City. He scored a total of seven goals over the course of the 2003/04 season, leaving the jury firmly still out on the Italian. There was talk of a move away from the Riverside, back to Italy with Empoli or Perugia, but the player insisted he wanted to become a success story in England.

source: soccernet