Jason Lawrance, 50, of Liphook, Hampshire, used two profiles to meet his victims from five English counties, Derby Crown Court heard.
He must serve at least 12 and a half years before being eligible for parole.
Judge Gregory Dickinson, said he was "devious, manipulative and highly dangerous to women".
Lawrance committed three attacks months after marrying his wife who he met via the site.
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The assaults took place between June 2011 and November 2014 in Derbyshire, Leicestershire, Lincolnshire, Northamptonshire and Cambridgeshire.
Lawrance, a self-employed builder, was found guilty on Wednesday of five counts of rape, one count of attempted rape and one count of sexual assault following a two-week trial.
Sentencing him, Judge Dickinson said: "I am compelled to the dreadful conclusion that you enjoyed raping women.
"After these terrible crimes you acted as if nothing had happened.
"Given the chance you will rape again. I do not know when it may be safe to release you into the community."
The court heard Lawrance's parents and three children were "devastated" by his convictions, however his wife is standing by him.
During the trial, jurors were told Lawrance used two pictureless profiles  - keepitstraighttoday and straightmanlooking  - to contact several thousand women, but was keen to talk to them offline.
Derbyshire Police began investigating in November 2014 after officers received a call from a woman who said her friend was raped by Lawrance.
Officers found that in June 2011 he drove a woman down a remote country lane near Crick in Northamptonshire and raped her in the back of his van.
Two years later he sent a woman a message saying "Boo! xx" 24 hours after attempting to rape her at her house in Spalding, Lincolnshire.
The jury was told he had consensual sex at a woman's house in Buxton, Derbyshire, in November 2013, but the following day raped her despite her "screaming hysterically".
He then sent her a text message reading: "When you were crying out for me to stop I couldn't, I'm so mad at myself xxx" and another saying "I was disgusted with myself for hurting you. I am so sorry. I am too rough for you xxx xx".
A year later, in 2014, he raped two women in hotel rooms in Leicestershire and Cambridgeshire.
Judge Dickinson said Match.com and police could learn lessons from the case after it came to light that four victims had previously reported his behaviour to the website but his profile was not removed.
Police said they hoped the case would get safety messages across for people using online dating sites.
Det Ch Insp Allison Rigby, from Derbyshire Police, said: "Jason Lawrance is a prolific, serial rapist who preyed on women."
Police said he contacted women who were divorced or widowed, and many were lonely and vulnerable.
During the trial it also emerged Lawrance was arrested by Lincolnshire Police in 2013 after one of his victims reported she had been raped at her home.
He was released on bail after officers said they had "insufficient evidence" to charge him.
Det Supt Rick Hatton from the force said they were constantly improving how they investigated rape and sexual offences, and said the case against Lawrance was strengthened once more victims came forward.
A Match.com spokesman said the company had the "most heartfelt concern" for the victims and it had a "zero tolerance policy" for reports of serious offences.
The firm said it had been unable to initially remove Lawrance's profile because the abusive messages had been sent outside their website.
Their statement said members were encouraged to communicate within the site where they have the technology to "spot unacceptable behaviour".
A "sexual predator" who raped five women and attacked two more after meeting them on internet dating site Match.com has been jailed for life.