Sastre joined the new Cervélo TestTeam for the 2009 season. He won the high mountain Stage 16 of the 2009 Giro d'Italia, which had been called the Giro's queen stage, after seven hours and twelve minutes. His decisive attack saw him break free from a group of general classification contenders to get to the summit of Monte Petrano just under half a minute faster than the group he left. After seeming off his form in Stage 17 of that race, Sastre rebounded with another solo ride to victory in Stage 19 to Mount Vesuvius.