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Wife won a PowerBook G4 at the Apple Store back in 2005 when they launched Tiger. Other than that, nothing, and I probably entered all together 100 times at various giveaways.
(the free iTunes song coupon doesn't count... only $1)
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I won a coconut in grade school, it was the first one I had ever seen with the husk on it.
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Almost.
I won a bunch of stuff in a raffle at one of those electronic booths at the 99 or 2000 Macworld in NYC. However it was one where you had to be there when they called your name. If you weren't they'd throw something else on the pile and pick another name. My boss and other colleagues were there looking for me but of course I was fecklessly wandering around forgetting the time the raffle started.
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Yes, but nothing that great. Although, I have had some decent jackpots with slot machines.
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I won concert tickets from a radio station.
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Does stuff you don't want count? One year (a long time ago) we entered a drawing because we wanted the second place prize - a cord of wood. We wound up winning the first place prize, a wood stove. It was the last thing we needed in our new house with the three fireplaces. After our son was gone from home, I won a trip to Disneyland for four. There were only two of us, and Disneyland was the last place we wanted to go. I think the nice lady at the travel agency let me take the money and use it for something else.