The then 20-year-old was at a dance party at Ferguson Bar on the Massey University campus at Albany with about 1,500 other people in March 2019.
He was kicked out of the bar and trespassed at about 11.30pm after having drunk up to nine bourbons.
Police walked him towards an area where there were taxis but he stopped and said "I'm not leaving", pushed two constables in the chest and tried to re-enter the bar.
He was arrested but refused to be handcuffed and was put on the ground where he thrashed his arms and legs in an attempt to break free.
When another police officer tried to handcuff him, Bailey punched him in the face, knocking him backwards.
The police officer, who is only referred to as senior constable Wilson, was left with a fractured nasal socket, swelling and a broken tooth. He was taken to the hospital where he spent the night.
At the sentencing, Bailey's lawyer argued for a discharge without conviction, claiming the conviction would affect future employment and travel plans.
But the Judge dismissed the application and sentenced the man to 80 hours of community work.
"I am satisfied the consequences of conviction were not out of all proportion to the gravity of the offending."
In May, Bailey's lawyer appealed against the conviction, asking for a discharge without conviction to be reassessed and submitting that Judge Paul had failed to address the mitigating factors.
"Bailey's youth was a factor the Judge should have taken into account, youths are more likely to act irrationally and emotively with impulsive and aggressive behaviour."
"Rehabilitation is important for young offenders," he said.
The lawyer described Bailey's efforts to rehabilitate himself, his remorse and how his gravity of reoffending was low.
In Bailey's affidavit, he claimed he tried returning to the bar to receive his credit card to order a taxi home, but in an attempt to explain his situation to the police, he became frustrated and touched the officers.
"I didn't intend to injure the constable at the time," he said.
But Justice Venning said that Bailey had many opportunities to de-escalate the situation and co-operate with the officers rather than reacting violently and aggressively.
"He was badly affected by alcohol and while he expresses remorse, his offending is still assessed as being moderately serious."
"While age may explain or mitigate the gravity of the offending in some cases, in this case, Bailey was intoxicated, which is not a mitigating factor."
Justice Venning noted how the conviction hadn't actually affected Bailey's employment as he had completed his apprenticeship and remains supported by his employer.
Justice Venning also stated his conviction didn't affect his travel, as after his conviction he had travelled with no issue.
The appeal was dismissed.
