On three days in July, John Pozzo showed up outside a woman's residence yelling and calling her vulgar names.
Each time, the 58-year-old man did this he was breaching a probation order that required him to have no contact with the woman and not be within 50 metres of her.
On Friday, he pleaded guilty to the charges, and Pozzo, who has been in custody since he was charged with the offences, was sentenced to 150 days jail.
With the credit he received for his pre-sentence custody he faces a further 27 days behind bars
His offences occurred on July 12, twice on July 14, and once again on July 15.
Police went to the woman's Second Line West residence at 8:45 a.m.on July 14 to check on her well-being, Ontario Court Justice Melanie Dunn heard.
Officers were told Pozzo had been there since 5 a.m. as well as on two prior days, assistant Crown attorney Stuart Woods said.
Police responded to similar accusations on July 15.
He told the court the accused has a four-page criminal record - the most recent offences occurring on Feb. 26 of last year - with numerous breaches and simple assaults involving the same complainant.
"He is to have nothing to do with her and is back before the court because he breached (the order)," Woods said.
The complainant is a victim of domestic violence, the offences occurred three days in a row, and a custodial sentence is required, the prosecutor said.
Walker agreed his client's record record is lengthy, saying "it is what it is."
Pozzo was involved in an accident in 1989 resulting in serious head injuries that others have said changed him, the defence told the judge.
Calling the guilty pleas a mitigating factor, Walker noted the accused had been denied bail and has been "a bundle of nerves" worrying about the sentence he is going to receive.
When she imposed the sentence, Dunn called Pozzo's record "very aggravating."
She also placed him on probation for two years with conditions to stay away from the complainant.