In 1999, Olano was back to defend the Vuelta title. In the prologue, severe rains put the late starters (including most of the GC contenders) at a big disadvantage, but Olano nevertheless managed to take 2nd place. In the stage 7 time trial, Olano won with a clear margin to main challenger Jan Ullrich, taking the top spot on the GC and the Yellow Jersey. Olano defended his lead through several mountain stages, but a crash on the stage to Alto de Angliru cost him a broken rib, and he was eventually forced to abandon the race.