Haha great thread - hoping there are some outrageous answers!
Worst I've done so far is place my £30 IASbet SNR on the Pittsburgh Penguins to win the Stanley Cup. IASbet said 2nd February 2011 on that page of the site, and I never thought to check it before laying the bet off at betfair (at odds of 8.2)
2nd Feb comes along, go to betfair and £225 still tied up in my lay stake - wikipedia it, and apparently the last possible date for the Stanley Cup final is June 17th
£225 tied up for 5 months. 2 months down. 3 to go!
Not quite 2 years:
Decided to start my Euro 2012 book a little too early, had a £50 freebie. Looking back now feel it was a silly move but think I was having withdrawal symptoms from my world cup book. Why I didn't do it on champs league or something I don't know. Now whoever can name the book from that screenshot will be champion of the world
Not mine, but a friend of mine had a bet several years ago that her Grandma would live to a greater age than the Queen Mum, when they were both still alive. The bet is still open
Just after Wimbledon 2009 I had E/W bet on US Open winner (concluded in September 2009). I put the bet on via oddschecker and as they messed up markets and I was guilty of not reading the ticket properly, my bet was actually on Wimbledon 2010 wiiner...
Did a bet on an outright hockey market (not NHL) at Betway with a free bet. Didn't realise that it was for the following year, but after doing so I didn't bother to lay it. Then a year later I noticed my balance went up a bit (Sadly only a £10 freebet)
A long time ago I once bet on would there be a total eclipse in year 20XX (I forget the year) and it was 1.01 on but I had checked and there definitely was going to be one = Patrick Moore had said so! So I lumped on, only a few weeks later did it truely dawn on me that I had a garunteed winner but the eclipse was in over a years time and I would have been MUCH better off just putting the £s into a savings account.
That was, foolishly, my longest ever future bet, it was about 14 months from when I placed it.
I regularly have bets for up to a year away on long term markets where I can make a book out of it, currently Championship winner market and also Champions League markets, which now settle quite soon but I started them up back in September 2010.
Have a plan and stick to it
Fuck me, where can you bet on eclipses? They're predicted so accurately that the slowing of the Earth's rotation has been calculated from 3000 year old Babylonian records for an eclipse that should've been in China.
I think many people have been in the "next Manure manager" market for more years than they'd like as well..