Complex sentence: Napravnik obtained her jockey license in 2005 at Pimlico Race Course, and won her first race as a licensed jockey on June 9 of that year, riding Small's horse, Ringofdiamonds.
Split into simpler sentences: Napravnik obtained her jockey license in 2005 at Pimlico Race Course. She won her first race as a licensed jockey on June 9 of that year, riding Small's horse, Ringofdiamonds.