James McMaster, 57, from Wakefield, was jailed for 18 weeks at Leeds Magistrates Court on Monday for breaching the terms of his Criminal Behaviour Order (CBO).
He was spotted drinking lager in the Sun Lane area of the Wakefield city centre on January 13.
After the hearing, police have said his latest sentence should serve "as a warning" to those similar orders, that breaching them can result in lengthy terms behind bars.
McMaster was served with a two-year CBO in January last year, over consistent reports of alcohol-related anti social behaviour in the city centre.
Inspector Helen Brear, of the Wakefield West Neighbourhood Policing Team, said: “Criminal Behaviour Orders are intended to protect residents from the kind of persistent anti social and disruptive behaviour which can cause real misery at a local level and the strong sentence given to McMaster in court makes it clear they do work.
“He has been involved in persistent anti social behaviour in the city centre related to alcohol for a long time now and has shown repeated disregard for the order imposed on him.
“We hope this sentence will give him opportunity to think about his behaviour and will be monitoring him closely on his release.”
Under the terms of McMaster's order, he was told he could only enter Wakefield city centre zone - bordered by Jacobs Well Lane, George Street, Bond Street, Queen Street and Stanley Road - for pre-arranged appointments, or when travelling through as a passenger in a taxi or on public transport.