Complex sentence: He has played several season on the tour, but has never made enough money in a season to retain his card, returning via the second tier Challenge Tour Rankings in 2005, having won the Panasonic Panama Open during that season, and qualifying school in 2006.
Split into simpler sentences: He has played several seasons on the tour, but has never made enough money in a season to retain his card. He regained privileges via the second tier Challenge Tour Rankings in 2005, having won the Panasonic Panama Open during that season, and qualifying school in 2006.