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Diamanti's first club, Prato, is located in the Italian city of Prato. The club was founded in 1919 and plays in the Serie B, the second tier of Italian football. Prato has won one Serie B title and one Coppa Italia. Diamanti played for Prato from 2003 to 2006, making 43 appearances and scoring 12 goals. He helped the club win promotion to Serie B in 2005.