I sometimes play scratchers. The best I’ve done is winning $50 on a $20 ticket. Best I’ve done with a machine game is $7 (Powerball, I believe.)
I generally head to the casino if I’m serious about doing some gambling. Scratchers are boring.
$474 when I got 5 out of 6 numbers in the Colorado lottery.
$250 from a $1 mega millions ticket
i was in line behind a guy who won $50,000 on a scratch off ticket a few years ago
Back when California’s lottery worked on the 6/49 system, I got several $5.00 wins (three matching numbers) a year, buying two $1 tickets a week. Once or twice a year I matched four numbers, worth a prize of roughly $50 to $80.
Since they’ve changed to the 6/52 (?) with vastly longer odds, the most I’ve ever gotten is a free replay. 
I really should stop bothering.
When my state started Quinto I bought a couple tickets for the first drawing and won $300. Haven’t won a penny on that game since. My mother hit 5 of the 6 numbers in the Lotto game twice and won $712 and $654.
I have purchased exactly one lottery ticket in my life. It won me $20, and I decided to quit while I was ahead. The store owner who sold it to me (and from whom I collected the $20) spent some time trying to convince me that I should take my winnings in additional tickets. He eventually forked over the money, with some mutterings about how I was “screwing up the system” with my insistence on a cash payout.
Grand total = $0. Oh, I guess you’ve got to buy tickets to win. 
Doesn’t sound weird to me. Four million just isn’t the sort of money it used to be…
Per the OP, from a scratch off? I won $25 on a ticket I didn’t even buy. I found a pile of scratched off lottery tickets when I was 16 or so across the street from a bar, and for some reason I decided to pick them up and check 'em. Sure enough, somebody had neglected to notice their $25 prize, so I cashed it in, and treated my friends to pizza.
$1,500 - back when that Illinois guy won that huge amount back in the 80’s sometime. I don’t remember the details.
My MIL hands out a bunch of scratch off tickets at Christmas and between my husband and I we usually get $20-30. I think the most from one individual ticket was $20 off a $2 ticket.
$500.00. I had a hunch on a 3 digit number, played it and won. It was about 10 years ago and was the only time I played the 3 digit number in the past 25 years.
I only buy tickets the day after a drawing so I can dream for the entire week. When I am in the States, I stay at my Mother’s house. So I let her check the tickets. I never win anything.
Or so she claims.
$1466
Figure $2 a week on the bi-weekly lotto draws since I turned 18, and that’s the amount I haven’t spent on voluntary taxes.