The law allows a person, in some circumstances, to withhold information from the public about their criminal convictions.
Justice Mathew Downs heard the man's appeal today.
"Would you employ a person with a history for sexual offending?" Justice Downs asked.
"The instinctive response is no."
The man's lawyer, Dr Roderick Mulgan, argued if his client was not granted a clean slate "word would be all over the city" once he applied to work in the aged care industry.
However, Justice Downs said: "I have difficulty with the submission that somehow there would be a bush telegraph."
Mulgan said letters in support of the man, who previously also lectured at universities, showed he had the "personal qualities" of an ideal person to work with the elderly.
"There is no such thing as a person presenting with no risk at all," he said.
The lawyer said Parliament had intended the Clean Slate Act be used for someone such as his client.
"If not this applicant then who? This is an excellent example of the sort of person Parliament had in mind."
He said employers find it difficult to look past the stigma of serious criminal offending.
"Parliament obviously intended that there could be somebody that committed a serious crime and yet went on to work in an industry where a serious crime [could be seen as a problem]," Mulgan said.
Justice Downs expressed concerns about visiting grandchildren at a retirement village, however, Mulgan argued the man should not be completely barred from places where a child may simply be.
"There will be children in the public library, there will be children in Cornwall Park," he said.
Letters from potential employers were "broad" and "merely says the employer would not employ the person with a serious or sexual offence", Justice Downs said.
He allowed Mulgan to refine the evidential basis of the appeal and submit material identifying the likelihood each employer would employ a person with the man's history.
The appeal was adjourned part-heard and will conclude at a later date.
