The attacks occurred in South Yarra, Elwood, St Kilda and Prahran.
After a rape of 2014, prosecutor Andrew McKenry said, Hartland told the woman, "You can call it Monica Lewinsky's dress."
The following year, in the pub, the woman escaped the cubicle, but Hartland took the panties and stuck it in the friend's face.
During a series of emotional declarations of impact victims read in court, a victim spoke of being objectified, devalued and manipulated by a man she compared to the "devil," whose mood swings fluctuated between displays of generous flattery and charm to anger. , abuse and behavior control.
"I feel absolutely raped in every sense of the word: emotionally, financially, physically and sexually," the woman said.
Three of the women were in court, but Hartland's fourth victim took his life this year.
The 44-year-old was raped at her home in 2014 and her brother said in a statement that "she could never come to terms with what happened," and went into depression.
The brother said that the impact of his sister's suffering was permanent, unforgettable and unforgivable, and asked Judge Paul Higham to consider the suffering of his family.
The other women said that her friend's death had increased her own trauma.
"She was a brilliant, bright person who should still be alive," one of them said. "My heart breaks for her family."
Two of the three women in court said they had considered suicide since the attacks.
McKenry said prosecutors had no evidence that a woman's suicide was attributed to rape.
Hartland, 44, pleaded guilty to three counts of rape and indecent assault. He also admitted harassing one of the women with text messages and distributing her intimate images without his consent, and violating court orders.
He pleaded guilty in October but remained on bail, despite the concerns of his victims, who were scared while he was in custody.
Earlier this month, he again admitted his crimes after withdrawing a request to change his claim.
His intent to try to plead innocent made the women even more upset.
Defense lawyer Greg Barns said the attempted change was based on Hartland's attempt to "delay the inevitable," and acknowledged that he faced a lengthy prison sentence.
Hartland met the women separately in Tinder, McKenry said, but in the run-up to each rape, the women told Hartland they did not want to be with him any more.
During two of the attacks, Hartland's ex-partner was sitting outside the women's homes in a car, McKenry said. There is no suggestion that she knew of the attacks.
Mr. Barns said that Hartland was in a relationship with the woman between 2010 and 2014 but he abused alcohol and drugs after his breakup and began using dating apps to hunt women.
She continued to support, Barns said, but was not in court on Monday.
Hartland wore a band on his left ring finger while he was in the dock.
Hartland's victims have spoken of meeting him as Dylan, and he lied about his jobs, hobbies and passions and became aggressive and evasive when his stories began to unfold. After his breakup, he said he would get hurt.
In court on Monday, the group spoke of going from strong, proud and independent women to living recluse lives and feeling isolation, shame, reduced value and fear.
"I felt as if my spirit had been broken and I fought to see how it would return to normal again," said a woman who moved in interstate but is determined to heal.
Another said that she thought that being stubborn and intelligent would always keep her safe, but her constant vigilance and fear made life difficult for her and her child.
"My son and I have the right to feel safe and we do not," she said.
Hartland has served two terms of imprisonment for two months to get in touch with two of the women while on bail, once screaming at one on the street and for the second time getting involved with one on social media.
McKenry asked the judge to consider Hartland's danger to women.
"This is the kind of crime that is very publicly aware," he said.
Mr. Barns said that Hartland was abandoned by his mother as a baby and made a state protection, and said his client reported that police had been abused as a child by men with whom he lived. He had already been diagnosed with narcissistic personality disorder.
Hearing what the victims say means "the coin has finally fallen," Barns said, and he was "broken" by the damage he caused.
But Judge Higham questioned whether Hartland had any insight or remorse in his dealings with a psychologist, where he had justified his crimes.
He will be sentenced May 10.
If you or someone you know needs support, contact the National Sexual Assault, Domestic and Family Violence Counseling Service at 1800RESPECT (1800 737 732), Lifeline 131 114 or beyondblue 1300 224 636, or Victim of Crime Helpline 1800 819 817.
Adam Cooper joined The Age in 2011 after a decade on AAP, the country's news service. E-mail or tweet Adam with his news tips.