Like his parents, Harry personally defied Voldemort three times before defeating him the fourth time: once in the Philosopher's Stone Chambers, once at the cemetery in Little Hangleton, and once again during the Battle of the Department of Mysteries. However, there were five previous encounters, if one counts the events of Harry's second year with Tom Riddle's Diary, though that was a memory instead of the real Voldemort, and the night his parents were killed in Godric's Hollow.