I once had £2400 riding on a hand of blackjack, 3 boxes of £400 with splits and doubles. Best hand was 17, against the dealers 4. Dealer pulled 8,A,A,2,A making 17 leaving me £2000 down. The thing that annoyed me was that on two hands I had doubled 11 and got an ace on both, yet the dealer, who to be fair to her did look rather sorry, still found three more.
Went the Casino one fine afternoon with £11k I'd won the night before. Lost it in less than 2 hours.
Stood at a roulette table for over 60 spins betting 2 and 6 neighbours by £5 and 17 by £10, £100 bet. In those 60 odd spins the ball didn't once land between 19 and 36, by which time I had lost nearly £8k as towards the end I'd started putting an extra £50 straight up on 17 as desperation set in. I also started covering the splits of 17, and hit none of those numbers either. I remember feeling rather numb sat at home watching a signed nature documentary at 4.50 am.
Still, it wasn't all bad luck. I fondly recall an occasion when I was around £4000 down on roulette, betting rather heavily on 0 and the neighbours, only for 15 to come in and repeat twice. This put me roughly £6000 up. The victory was marred somewhat by the pit boss who had a pop at the croupier for cheering excitedly as 15 came in the 3rd time. Knowing I was unlikely to be barred at this point unless for very good reason I told the pit boss he was a bitter old cunt.
I put a ten pound 9 team accumulator on once, and all teams won, netting me around £1650. This was significant because within 2 days I had managed to turn it into nearly £20 grand in Stanleys Casino, Gt Yarmouth. Well within a week I managed to turn that £20 grand back into a tenner.
A few years ago Arsenal were playing Bolton, and were 5/6 at Corals. You never forget the price when you have a big football bet, whatever anyone says. I put £1500 on Arsenal, hoping to pinch a sweet £1250. After around 70 mins Arsenal were 2-0 up, and I sauntered down to the bookies only to find Bolton had scored twice in the last 10 mins to earn a draw. The smug prick behind the counter could barely disguise his delight.
Going back a good 15 years a friend had a huge Accumulator on several teams, and it all rested on Arsenal to beat Sheff Utd for him to earn around £150,000 which was a considerable amount of money in those days, as indeed it is today, just not as much, if that makes sense. Anyway Arsenal were 1-0 up, and in the latter stages Arsenal missed a penalty, and then conceded a goal straight afterwards, or something along those lines. Every time I see him he tells me that story as though i've not already heard it over 100 times.
3 Card Brag in the Casino... Was once £7000 down playing £50 on the front, £100 on the back. Never even saw a pair in that time, until 10 mins before closing when I got 3 prials in 5 hands, and some flushes etc. Ended up £400 up on the night, which I spent on a prostitute and some cocaine.
2 or 3 years ago a friend of mine who loves to hammer short prices put £1400 at 1/7 on Roger Federer to beat the hard-hitting Ivo Karlovic. I told him it was a shit bet but he loves sweating over his bets. For a laugh I put £100 on Karlovic, and was laughing long into the night when he beat Federer. Sadly for my friend he went on tilt that night and lost another £2000 throwing money at some obscure betting opportunities such as Danish league football and American Ice hockey.