Sheffield Crown Court was told how David Bysouth broke into both businesses on the evening of March 12 this year.
Bysouth broke into the Mydentist surgery in Laughton Road, Dinnington first, where he gained access to the building by smashing the front window.
"They found that a Cancer Research box, along with charity wristbands, had been taken," said Louise Gallagher, prosecuting.
Bysouth, of Moorhouse Drive, Thurcroft left traces of his blood behind near to where he smashed the glass to enter the surgery, the court heard.
The 36-year-old then broke into the Age UK charity shop, also located on Laughton Road, where he stole £57 from the shop's cash float, as well as clothes, jewelry and a charity box.
Ms Gallagher told the court that Bysouth gained access to the shop by smashing its front door, where traces of his blood were found once more.
"The dentists' surgery said they were disappointed someone would steal funds from a charity, and Age UK thought it was pretty low to steal from a charity that helps people," added Ms Gallagher.
South Yorkshire Police arrested him the following morning, after receiving intelligence from a member of the public, and he made 'full admissions' when interviewed, the court heard.
Bysouth, who has 21 offences of theft on his record, pleaded guilty to two counts of burglary from a non-dwelling at an earlier hearing.
Defending, David Horne, said Bysouth's story of stealing to fund a drug habit was one that the courts hear 'time and time again,' but said he had made him aware that should he be given the opportunity of a suspended sentence he must not 'throw it in the court's face'.
Judge Paul Watson QC sentenced Bysouth to 16-months in prison, suspended for 18-months, ordered him to complete a 25-day rehabilitation activity requirement and a 12-month drug rehabilitation programme.
Judge Watson said: "You stole so you could feed your drug habit. I accept that it's something that has plagued you for many, many years.
"The pre-sentence report argued that sending you to prison may expose you to more drugs."
He added: "If you come back in front of me, and I'm reserving this case to me, I will send you straight to prison, starting with the 16-months.
"I hope you will prove yourself, that you will manage to turn your life around over the next 18-months, and take advantage of the help you are going to get."