The former Arsenal and Liverpool ace revealed that pals would pay each other "rent" if they romped with the same woman — and rated them like properties on the board game.
He said: "We used to call it Monopoly. You have your properties, all different standards. You’ve got Mayfair and Old Kent Road (the lower standard – no one wants to be there)".
Pennant wrote about the warped game in an extract from his new book Mental: Bad Behaviour, Ugly Truths And The Beautiful Game, which is being serialised in The Mirror.
He admitted he and his Premier League pals played "for years" — adding: "Most of the lads were involved".
He wrote: "If I slept with any girl and then any of the other lads slept with her afterwards, they would have to pay me 'rent': if she was Mayfair, they would have to pay me £100; for Old Kent Road it would be £14."
Pennant added that "Old Kent Road" meant less attractive women — while the "Mayfair" title was reserved for stunners.
The winger, part of Rafael Benitez's talented Liverpool side that just missed out on Premier League glory in 2008-09, also explained why his career stalled.
When asked by Rafa what was holding him back from becoming a top player, Pennant responded with one word: "Chicks".
Pennant, 35, is now married to webcam performer Alice Goodwin who gives raunchy displays to online fans.
But he boasts of having played the field as a young footballer.
He wrote: "I would get a flock of birds, loads of girls. It went on from there.
"You want to go out every week, pulling different birds, doing God knows what until all hours of the morning."
Pennant was once engaged to glamour model Amii Grove — but admitted she dumped him when she caught him playing away from home.
He wrote: "I gave her a big engagement ring and then she caught me cheating again and that was the nail in the coffin. She auctioned it off on eBay."
He also dated Hollyoaks star Jennifer Metcalfe. There is no suggestion his depraved Monopoly 'game' involved her.
Pennant, who began his footballing career as a youth player at Arsenal, has also lifted the lid on the exploits of former teammate Ashley Cole.
In one explosive extract he claimed that Cole had a girlfriend when he began dating his now ex-wife Cheryl.
And left-back Cole even locked the unnamed woman out of his flat while he enjoyed a date with the Girls Aloud star.
But his closeness with Cole doesn't end there — as Pennant revealed he even had threesomes with his pal and other women.
In one grim passage Pennant admits "high-fiving" Cole while they both romped with a woman — whose name he has now forgotten — at a Canary Wharf pad.
He bragged: "We had a little tea break and then went at it again. They just don’t care."
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