Last June, he went on a rampage - harassing his former girlfriend and her teenage daughter, attacking their neighbour, and assaulting a police officer.
While out on bail three months later, Muhammad Al-Farouk Alwi, 33, slashed two strangers with a chopper.
Yesterday, he was jailed for four years and ordered to receive six strokes of the cane after pleading guilty to causing grievous hurt, assaulting a policeman, behaving in a threatening manner towards the mother and daughter, causing hurt to their neighbour, and causing grievous hurt with a deadly weapon.
Al-Farouk was living with his girlfriend, 49, in her flat at Block 19, Jalan Sultan, near North Bridge Road, until she ended the relationship last May.
On June 15, he returned to her home at around 1am, where he shouted for the woman and her 17-year-old daughter as he banged on their front door.
Their neighbour, Mr Sher Kuan Hock, 57, was jolted awake and when he stepped outside his flat to investigate, was punched by Al-Farouk on his right cheek.
Three hours later, Al-Farouk punched Mr Sher's abdomen as he returned home after receiving outpatient treatment at Tan Tock Seng Hospital, where he was found to have a fractured nasal bone.
Twelve days later, two uniformed police officers were on enforcement duties in Lorong 10 Geylang when they spotted Al-Farouk behaving suspiciously. One of them caught him in a bear hug from behind as he tried to run away, and he bit the officer's right forearm.
Al-Farouk was out on bail when he used the chopper to attack two men in Jurong at around 4.40pm on Sept 24 last year, over a cigarette.