Bala Kuppusamy was also ordered to be caned the maximum 24 strokes on Tuesday.
The serial predator had been to prison twice for rape, and both times, went back to assaulting women just 1 1/2 month after his release.
His lastest crime spree took place between April 27 and June 10 last year, targeting women who were walking alone at night.
He would punch his victims, aged 16 to 34, into submission and demand that they hand over their money.
In some cases, he dragged the woman to secluded spots and sexually assaulted them.
He pleaded guilty to three counts of robbery with hurt, four counts of sexual assault and two counts of aggravated molest.
Describing Bala as a 'menace to society', Deputy Public Prosecutor Francis Ng urged the High Court to jail him for between 40 to 45 years.
Justice Tay Yong Kwang agreed that with his 'appalling' criminal history, he is 'not fit to live in society'.
'Too many females have suffered because of this merciless, marauding monster for whom liberty is a licence to rob, rape and ruin the lives of innocent females,' said the judge.
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