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By the end of Season 6, he's been stabbed in the back in All Hell Breaks Loose Part 2 in Season 2, he gets struck by lightning in Wishful Thinking in Season 4, Anna stabs him in the stomach in The Song Remains the Same in Season 5, he gets shot by angry hunters in Dark Side of the Moon in Season 5, and he falls into Lucifer's cage in Swan Song in Season 5. So he has died 5 times so far if I counted them all correctly.

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Q: How many times do Sam Winchester die?
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