The ex-Arsenal footballer, 35, claims his former teammate had locked the unnamed woman out of his flat while he enjoyed a date with the Girls Aloud star.
In an extract from Mental, published by the Mirror, Jermaine says the pair first got chatting outside the apartment block they shared in North London in 2004.
Cheryl was with bandmates Kimberley Walsh and Nicola Roberts when she commented on Ashley's "unlucky" Euros campaign and they swapped numbers.
The pair began meeting up and according to the excerpt, Cheryl started calling round at his apartment – warning them all to "keep it quiet".
Jermaine, who we revealed is set to join the new series of CBB, writes: "Then, one day, Cheryl was round his place with him. The door was locked from the inside. He’d kept the key in the lock so no one could get in.
"His girlfriend at the time had a key. She was trying to get in, calling him, going mad because she knew someone was in there. She was calling all the lads. We were ignoring her calls, we knew what was going down."
He added: "Cheryl and Ashley inside were probably looking at each other thinking: 'What’s going on?'"
In his book, he also revealed a warped footballers' "Monopoly" game where they rated women and paid each other "rent" for sex with them.
Admitting his teammates are "embarrassed about it now", the player explained they got "carried away" because of the amount of attention from girls.
Jermaine also claims he spent years trying to impress Cheryl's pal Kimberley – but she wasn't interested.
She was dating her now-husband Justin Scott at the time but the footballer says he continued to send her texts telling her she was "amazing".
He admits despite her protests he "never gave up" and believed "she was the one".
Cheryl, who was at this point known by her maiden name Tweedy, married Ashley in 2006 after a year-long engagement and were one of the UK's most high-profile couples.
However, during their marriage, the two were rocked by a string of infidelity allegations against the former Chelsea defender and the two finally divorced in 2010.
Ashley has since been in a four-year relationship with Italian model Sharon Canu and the couple have two children together.
Former Arsenal, Liverpool and Stoke City winger Jermaine also discusses his dad Gary's addiction to drugs in the tell-all autobiography.
Earlier this week, SunSport reported on the gang culture the 35-year-old grew up in, and how he avoided getting caught up in a murder investigation.
- Mental: Bad Behaviour, Ugly Truths and the Beautiful Game is out in hardback on Thursday
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