Stone Cold to win the 2001 Royal Rumble at 4/1 at Hills.
Actually - no I never did put that on and have regretted it ever since.
First bet was probably some mug football acca. First golf bet I would actually have been 22 and it was for a stake of around 20p e/w on I think Brett Quigley in the 2003 Greater Milwaukee Open.
Came in the places and I remember having a lengthy email back and forth with victor chandler about how I thought they'd incorrrectly settled it and short changed me to the tune of 14p or something.
No doubt they thought I was taking the piss but I genuinely wasn't!