Complex sentence: On 22 October 2006, he played his 300th Serie A match, in a 0--0 tie against Siena; he had played first Serie A match on 8 September 1993.
Split into simpler sentences: On 22 October 2006, he played his 300th Serie A match, in a 0--0 tie against Siena. He played first Serie A match on 8 September 1993.