The 500 winners will be selected at random from those fans whose account is linked to their Football League club, and who have bet £1 or more in September.
This December, Sky Bet will give one club a £250,000 Transfer Fund to spend on new players in the January transfer window.
Fans who bet with Sky Bet will earn tokens for their chosen club, before one token is drawn at random on December 8.
The lucky fan will win the £250,000 transfer kitty for their club, as well as pocketing £5,000 for themselves.
Sky Bet Sponsorship Manager David Tweed said: “It’s getting to the point in the season where signing up to the Sky Bet Transfer Fund could make a real difference to your club’s season, come January.
“With just over two months until the draw, there’s still time to build up a good share of Transfer Fund tokens.
“And you could also pocket yourself a £10 free bet just by signing up.
“If you’re already a Sky Bet customer, you can link your account with the club of your choice at any time.
“If you’re not yet betting with Sky Bet, there’s still time and you can claim a £30 matched bet when you open your account!”
To sign up for the Sky Bet Transfer Fund and start collecting tokens now, visit www.skybet.com/win
Full terms and conditions can be found on the Sky Bet Transfer Fund Website.