On both occasions, Caelen Hartford was bizarrely found not to be wearing shoes when police arrested him.
Prosecutor Vincent Blake-Barnard said the 26-year-old first entered the Esso garage on Armley Road in Armley on October 20 last year, and asked the employee for a pack of cigarette papers, saying he would pay for them later.
After being refused, Hartford walked around the counter and picked up ecigarettes and tried to walk out, but the worker pressed the panic alarm, effectively locking the door.
Hartford then walked back to the worker, struck him in the face, forced his face towards the till and made him open it, taking around £100. He also threw the ecigarettes on the floor, and left.
He was found by police heading towards the city centre barefoot a short time later, but only had £20 on him, saying he gave the rest away.
He then caused criminal damage to a police cell at Elland Road station by flushing a code of practice book down the cell toilet and causing a flood.
Having been bailed, nine days later he broke into the Coral bookmakers on Harper Street in Leeds in the middle of the night, throwing a concrete slab through the window.
As the police arrived they caught him with £20 he took from the charity box in the shop. Again he was shoeless.
Admitting a charge of burglary, robbery, and criminal damage to the police cell, he also admitted four counts of assaults on prison staff during the time he has spent on remand since, most of which involved him spitting at officers.
Mitigating, Satpal Roth-Sharma said Hartford had been smoking cannabis since he was 13, started taking cocaine at 19 and now suffered from drug-induced psychosis.
She said: “He previously sought help but has an addictive personality and falls back into his old ways quite quickly.
"He simply can’t recollect committing these crimes. They were out of desperation for drugs, with little or no planning.”
Hartford, whose previous address was Well Home Mead in New Farnley, has been in custody since October.
Judge Geoffrey Marson QC accepted Hartford’s remorse and gave him a three-year jail term.