Complex sentence: Sacked six times in his career, he remained unemployed after a good season with Reggiana in 2004/2005, ended in fifth place despite serious financial troubles in his club which then led to its cancellation.
Split into simpler sentences: Sacked six times in his career, he remained unemployed. After a good season with Reggiana in 2004/2005, he ended in fifth place despite his club's serious financial troubles, which then led to its cancellation.