Retired Judge Ralph Steinberg ordered Strawberry to serve prison time for his 1999 arrest on drug and solicitation of prostitution charges.
Strawberry, 40, was kicked out of a drug treatment center in March where he had been serving his time after counselors said he broke rules, including having sex with a resident and smoking.
The former major league star has not used drugs for more than a year.
Strawberry had fought previous attempts by the state to send him to prison, successfully persuading Hillsborough Circuit Court Judge Florence Foster to order him to drug treatment instead.
Strawberry, a former New York Yankees outfielder and eight-time All-Star, has violated his probation six times.
Last year, Foster had suspended an 18-month prison sentence for Strawberry provided he complete the program at Phoenix House in Ocala.
Prosecutors had urged Foster to send Strawberry to prison after he violated house arrest at a Tampa drug treatment center by escaping on a cross-state drug binge.
Foster, however, sided with Strawberry's attorney and doctors who said the former slugger needed medical care for his cancer and mental health services not available in Florida prisons.
Foster, who became the target of public criticism when she opted to send Strawberry to treatment, is on medical leave. The judge announced last week she is suffering from multiple sclerosis which is affecting her ability to preside over cases.