Complex sentence: He signed a two-year scholarship deal with Chelsea prior to the beginning of the 2009-10 season and helped the Blues' youth team win the FA Youth Cup for the first time in 50 years.
Split into simpler sentences: He signed a two-year scholarship deal with Chelsea prior to the beginning of the 2009-10 season. He helped the Blues' youth team win the FA Youth Cup for the first time in 50 years.