‘19 Nadal with a season record of 58W-7L and reached 3 GS Finals (AO, RG, USO) winning 2 (RG & USO) ‘99 Agassi with a season record of 63W-14L and reached 3 GS Finals (RG, W, USO) winning 2 (RG & USO) They both ended the year, as World No.1. So the real question is, who wins?