Dean has died thousands of times. In episode 11 of season 3 (Mystery Spot) Dean died thousands of times because Sam kept reliving the same day in which Dean dies over and over again as a cruel prank played by the Archangel Gabriel (pretending to be a trickster). Dean then died again at the end of season 3 when he was mauled to death by one of Lillith's Hell Hounds and was sent to Hell.
During season 5, Dean and Sam died again at the hands of two hunters who were angry at Sam for kickstarting the Apocalypse. This time we went with Dean and Sam to heaven where they were informed by Ash that they both have been there many times before but the Angels keep wiping their minds so they don't remember.
Dean did accidentally go to Purgatory with Castiel when he and Cas killed Leviathan Dick Roman, but neither were dead and both escaped separately.
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The answer depends on how many times a die is rolled and whether it is a fair die.For a single roll of a fair normal die, the answer is 2/3.The answer depends on how many times a die is rolled and whether it is a fair die.For a single roll of a fair normal die, the answer is 2/3.The answer depends on how many times a die is rolled and whether it is a fair die.For a single roll of a fair normal die, the answer is 2/3.The answer depends on how many times a die is rolled and whether it is a fair die.For a single roll of a fair normal die, the answer is 2/3.
1/6 of 300 = 50 times.
Gerard. Alice. Dean. Gil
If you were really unlucky, infinitely many times! The probability of that happening is very tiny but it is not zero.
The probability is about 43 times, though you cannot be certain, so there is no definitive answer.