Edward Dowlan, who changed his name to Ted Bales after serving his first child sexual abuse sentence, was sentenced to seven-and-a-half years jail on Thursday.
He was imprisoned for nearly a decade in 1996 for offending against 11 students, and for six years in 2015 after he admitted the abuse of another 20 students.
His latest sentence comes after he admitted more than 30 new charges relating to the abuse of 19 boys between 1971 and 1988.
Dowlan was then aged between 21 and 38 and was working as a teacher.
Those he abused were all under 16 - some were as young as eight.
"Their statements make it perfectly obvious that you inflicted on them individually and collectively a lifetime of damage and misery,"Â County Court Judge Gregory Lyon said on Thursday.
He said he wouldn't refer to them as victims, because they deserve much more than a label.
"I commend you for your courage and integrity in coming forward and making what has been a public bearing of your souls and life experiences," he told many who watched the sentencing online.
"I cannot imagine the courage it takes to do so."
Dowlan offended against some of his students on multiple occasions.
Some of the offending happened in a classroom at Cathedral College in East Melbourne. Other offences happened at Ballarat, Geelong, Anglesea and Warrnambool.
Two students were abused on a school bus, others were preyed upon in toilet blocks, change rooms and after being sent to Dowlan for misbehaving in class.
"Do you love Brother?" Dowlan asked one of the students while abusing him.
Judge Lyon said Dowlan's crimes were premeditated and sexual gratification was the predominant reason behind it.
His prospects for rehabilitation were constrained by the fact he doesn't have and has never expressed any remorse for his offending, the judge said.
Dowlan, 72, left the Christian Brothers in 2008. His offending was known as early as 1974.
Cardinal George Pell has said a boy "mentioned it casually in conversation" to him, but did not ask him to do anything.
Dowlan will be eligible for parole in November 2026.
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