The victims of London taxi sex attacker John Worboys have won a High Court bid for compensation from the Metropolitan Police.
Mr Justice Green ruled on Friday that the Met was liable to the two women, who were seriously sexually assaulted, for failures in its investigation.
One of the women, identified only as 'DSD', was the first of Worboys's victims to make a complaint to the Met in 2003.
The other, known as 'NBV', contacted them after she was attacked in July 2007.
Both women alleged at London's High Court that the Met had failed to conduct a reasonable and efficient investigation into the assaults upon them - and as a result, failed to apprehend and secure the conviction of Worboys for an unreasonably long period of time.
Worboys, who was jailed for life in 2009 for 19 offences, carried out more than 100 rapes and sexual assaults using alcohol and drugs to stupefy his victims between 2002 and 2008, Mr Justice Green said.
He ruled that damages would now be assessed.
Both DSD and NBV brought their claims under Articles 3 of the Human Rights Act, which relates to 'inhuman or degrading treatment'.
DSD said that she had suffered a depressive disorder as a result of her treatment by officers during the 2003 investigation, while NBV claimed that she had suffered serious distress, anxiety, guilt and an exacerbation of post-traumatic disorder and depression as a result of her treatment during 2007.
The judge said Worboys was clinical and conniving and the effect upon the women was "profound".
"I have learned that the effects of the assaults have stayed with them in a variety of ways over the ensuing years, manifesting themselves in depression, feelings of guilt, anxiety, and an inability to sustain relationships, including sexual relationships," he said.
"That trauma has to be multiplied one hundred fold, and more, to begin to have a sense of the pain and suffering that Worboys' serial predatory behaviour exerted upon his many victims.
"But their feelings are not the end of this circle of misery because, as was evident from the psychiatric and other evidence, the effects rippled throughout the victims' families and their respective circles of friends."
He said the Met was liable to both women for breach of the Human Rights Act in relation to the period between 2003 - which coincided with the first complaint to police - and 2009, when Worboys was tried.
"In this case I have identified a series of systemic failings which went to the heart of the failure of the police to apprehend Worboys and cut short his five-to-six-year spree of violent attacks," the judge said.
These included a substantial failure to train relevant officers in the intricacies of sexual assaults, and failures to interview vital witnesses and collect key evidence.
In a statement, the Metropolitan Police Service said that the case had raised "important arguments regarding the boundaries of police responsibility and liability".
"The MPS has previously apologised for mistakes made in the investigation of rapes committed by Worboys," it said.
"The judge acknowledged that the failings in this case were very much historic; a recognition that in the interim we have made important and significant changes to the way we investigate rape, which remains one of the most challenging and complex policing issues.
"We will now take time to consider the judgment in full."
Additional reporting by PA