The first of the terrifying incidents took place at around 4.25pm on December 4 last year, when 16-year-old Harvey Simpson began shouting at a woman he was walking behind on Kent Road, Meersbrook, Sheffield Crown Court heard today.
The woman turned round to see Simpson holding a kitchen knife with a 15cm blade, who then told her: 'give me everything you've got,' said Carl Fitch, prosecuting.
He added: "All she had was £5, which she handed over. As she did this he was holding the knife to her stomach. After handing him the money, he walked away."
Simpson struck again 50 minutes later, when he came out of a wooded area off Fraser Crescent, Woodseats and began pursuing a 56-year-old man who was walking along the road.
Mr Fitch told the court how Simpson's second victim 'quickened his step' in order to escape him, but Simpson caught up with him and the man turned round to see Simpson 'holding a chef's knife with a 12-inch blade'.
"The defendant said: 'give me all your money'. The complainant had no money on him, so turned out his trouser pockets in order to show him. The defendant said: 'These are difficult times, mate' and walked off," Mr Fitch said.
At around 5.25pm the following day, Simpson, of Hempton Road, Woodseats approached a woman from behind as she was walking along Woodbank Crescent, Meersbrook.
"The defendant said: 'Give me all your money'. He had his hood up and was holding a large glass bottle over his head," said Mr Fitch, adding: "The complainant said she would give him £10 as long as he didn't take her bag or her phone. The defendant took the money, and in a bizarre twist, shook the complainant's hand and said sorry."
Then at 6.45pm that evening, Simpson emerged from another wooded area near to Smithywood Crescent, Woodseats and jumped out at an on-duty postal worker, with a knife in his hand, and demanded money from him.
"The man offered his phone, but the defendant said he wanted his money. The complainant gave him £5, the only money he had, and the defendant ran off."
Mr Fitch said Simpson struck for the final time at 7pm, when he approached a pregnant woman walking along Rushdale Road, Meersbrook while holding 'some sort of blade'.
He said: "Simpson had his hood up, and pointed the knife to her stomach, and said: 'Give me your purse' and moved the knife closer to her stomach. She screamed and started to run away without looking back."
Simpson was arrested on December 6 last year, and admitted to three counts of robbery, two counts of attempted robbery and four counts of possessing a blade at an earlier hearing.
Mr Fitch told the court that Simpson committed the offences during a 'drug-fueled episode."
Ian Goldsack, defending, said Simpson was of 'previous good character' and had pleaded guilty at the first opportunity, despite having 'no recollection' of committing the offences because of the drugs he had taken.
The judge, Recorder Jeremy Barnett, said he believed Simpson had done 'everything possible that could be done to demonstrate that custody isn't necessary' and adjourned the case for three months to see if Simpson could continue to make good progress with his rehabilitation treatment and the probation service.
He said: "I've got a responsibility to you..but I've also got a responsibility to the public to make sure people don't walk round Sheffield with knife under the influence of drugs, not knowing what time of day it is and walking off with people's phones.
"I want you to write to me to explain how, for a short period, you went off the rails; and what you can do to ensure this never happens again."