Peter Ramsey, 26, who gave a false name online, punched the young woman to the ground, ripped off her tights and raped her on the stairwell of the flats where she lived with her mother.
The trainee personal trainer left the 27-year-old woman - whom he met on Plentyoffish.com - "unrecognisable" with 21 injuries from punches and kicks.
One blow was so hard it knocked out her front teeth.
After the attack he took her handbag and even used her tube travel card to get home.
Yesterday he was jailed for 12 years by Judge Patricia Lees at Inner London Crown Court for the "predatory" and "callous" attack.
"She was a trusting and genuinely delightful young woman whose life will be altered forever from what you did to her," the judge told him.
After the attack the police warned about the dangers of online dating and warned people to be cautious, and "thoroughly vet" those they intend to meet.
Ramsey and his victim had spent four days chatting on the dating website - which claims to be 'responsible for more dates and more relationships than any other dating site' - before arranging to meet for drinks in South London, last August.
"He seemed like a nice guy", she told the court.
"The date was going well. I thought we had a lot in common."
The pair met for drinks at 7pm in Brixton, south London, and went for dinner before hailing a cab to the woman's flat in Clapham Common.
But when she pulled back from a kiss at the front door, she said, he "switched".
The court heard Ramsey pinned her against the wall in the communal entrance hall, punching her repeatedly in the face until she slumped to the ground.
When she tried to scream for help, he put his hand over her mouth and pinched her nose shut, while continuing to hit her with the other fist.
He then threw her down the concrete stairs before raping her.
Leaving her bleeding, he stole her handbag and used her Oyster travelcard to board a nightbus and escape.
She said: "I thought I was going to die."
Once Ramsey had left, she managed to call for help and was discovered by a member of the public.
Her own mother, who heard the screams, came out of her home moments later to find her disfigured daughter.
The next day, Ramsey attempted to call the woman and left two voicemail messages telling her he was sorry, he had sobered up and felt something had happened that "wasn't good".
He was arrested a week later thanks to a DNA match and CCTV footage showing him on a bus near the scene.
Initially he told police the sex had been consensual and that he had witnessed her arguing with another man who had beaten her.
During the trial, he told jurors had been out with "hundreds of women" and did not need to rape because he could "get anyone he wanted".
He was found unanimously guilty following a trial.
Following the trial, DC Richard Huggins said: "I feel relieved that somebody like Ramsey who had access via the internet to so many women, is now safely behind bars.
"This woman was unrecognisable after the attack, compared to the woman who gave evidence.
"'I have been in the police for 14 years and these were some of the most shocking facial injuries I have ever seen."