Cr Bill Acklin - a city councillor and performer who runs Bill Acklin Entertainments - secured the contract to provide entertainment for Rugby World Cup revellers at the Town Hall.
However, Cr Acklin told the Otago Daily Times he had done everything right in seeking clearance for the work from the Office of the Auditor-general (OAG), which confirmed no conflict of interest existed.
"That was just a safeguard. That confirmation has come back from the Auditor-general, so the approval has been given," he said.
However, Cr Acklin said, as an entertainer, he was "very disillusioned" by the continued questioning of his dual role.
"I was an entertainer before I was a councillor and I think I should be able to go ahead and continue in my entertaining role ... without criticism of some sort of underhanded nonsense going on, because there's not."
The latest questions came after his company also secured the $40,000 entertainment contract for the New Zealand Masters Games last year, while he was a Masters Games board member.
It was the sixth time since 2000 Mr Acklin's company had won the contract, each time worth $30,000to $40,000.
He denied any wrong-doing at the time. He had taken no part in entertainment contract deliberations and votes as a Masters Games board member, and had also obtained OAG clearance for the work.
Cr Acklin's latest Rugby World Cup work included performances by his five-piece covers band, stage production work and sound for the town hall's big screen, using his company's equipment.
That meant there were "synergies" that saved money for the fan zone's operator, Dunedin Venues Management Ltd.
DVML chief executive David Davies confirmed when contacted "a couple" of alternative options had been considered, but Cr Acklin's offer "represented good value for us".
Neither Mr Davies nor Cr Acklin would discuss details of the contract, except to say it was "performance-based".
Cr Acklin said it was covered by proceeds from the fan zone's operation and was not ratepayer-funded.
Mr Davies said DVML had also sought advice from council staff and the OAG "to make sure that we weren't doing anything we shouldn't have done".
"Had there not been a process to go through, then I think everyone would have been in a position to say, `Look, it doesn't look and feel right.
'"But, given we went through the process, I'm pretty comfortable that we got good value for money."