Probably not what you had in mind but I won twice in my country's version of HQ Trivia, total of about $60 usd.

They kept saying that there were some technical problems and delaying payment. In my country that amount is not nothing but also not a ton of money so I really didn't bother too much. My brother on the other hand kept calling and emailing until I guess he was a bigger nuisance than it was worth and they finally paid.

PayPal took an unreasonable chunk, I gave my brother like half for his efforts and I kept like $20. All things considered probably a good way to spend those 20 minutes playing.

My family won a lifetime supply of chunky peanut butter in a seat number lottery at a baseball game. It was 12 large jars of peanut butter (36 oz) for 20 years. Needless to say we asked them to not send anymore after the first year. I hate chunky peanut butter now.

As a little kid we won second prize in a national cereal box contest, a “treasure chest of board games.” We received a thin paper game board with plastic tokens we had to pop off. Someone sued, because we got sent a letter and and two $1 coupons off Post cereal.

One might say my cynical view of large corporations started early.

Edit: I’ve also won a snowboard from Mountain Dew in college, but that was an actual snowboard.

I won $900 playing deal or no deal at a bar. Maybe it was just luck, but I did feel I could read the host who claimed not to know the outcome of any given deal. Watching him before my ticket was drawn to play, I notice he seemed to lead people to their decisions a bit. It also occurred to me a few times while playing that he was at least occasionally leading me into correct choices.

Anyhow, the last deal comes up and I make up my mind on if I will take the deal or not. Then I figure I'll let my friend choose. Her decision was opposite mine. It was the only wrong deal in the game.

Afterward a bunch of people in the bar bought us drinks. I split the winnings equally with my two friends. We agreed to do so when they bought me a raffle ticket to play because I don't gamble.

Nothing but losers here....

I had a Redmi phone made by Xiaomi. They conducted a giveaway on Twitter and I won it. I was shocked by seeing it, as it was the first time I won anything.

Received the same model phone in a month time. I gave it to my sister.

My phone was stolen after 2 months. So I felt like if you don't spend money and "earn" something, it will leave you soon.