What's the most money you ever won from a bet?

$600 on Super Bowl squares

 

Probably $35 playing knock

 

Same, also had the over 4.5 wins! Only won $200 though, kudos to you for believing in this team more than I did.

 

In High School, I stuck my head in a Chick-Fil-A used peanut oil bin (room temp) and won 3 cases of Moosehead from 3 friends that bet me I would not do it. The ride home was kind of nasty especially since I had to stop and get gas.

 

I have never been one to gamble as I always felt I worked to hard for my money(with the exception of a $2 Nassau in golf no automatic presses

 

I’m not gonna give the specific amount, but many thousands when I placed a pretty sizable bet before opening week on the 2006-2007 Gators to win it all.

 

$600 on a four team $50 parlay.

 

$250,000. Bought a Mustang and a double wide! Lost it all on meth and hookers!

 

Straight up dollar for dollar. $1,000.
Dude thought because he's a neurosurgeon that he couldn't be wrong. He went straight to Google. Upon learning he's lost immediately started with the "oh I got things mixed up."

Sure did. That's why he lost.

 

5K on a bet that lost. I placed 500 $ on the gators at 60 to 1 to win the NC . They won the their first 10 games(?) and a Miami fan( SO. AM. importer-my perception) asked me what I wanted for the the bet. I said 5K because i had no intention of selling. He gave me said amount and I wasted it all as was appropriate.

 

According to my junk e-mail file I have won the Irish Lottery at least twice and have an African prince that will go halfsies with me if I give him my bank account info so he can move $15,000,000 out of his country!

 

I bet $20 on an Exacta at Del Mar last summer. Saw my two horses come in 1-2 and went up to cash in my ticket. I saw $1700 on the register. I told my wife behind me that someone before us just hit it big. Turned out that my picks, which I based by their names, were a 85-1 shot to come in 1-2. Pure luck all around!