Toronto police say the robberies happened in October 2019 at convenience and cellphone stores.
Investigators say the disguised suspects were armed, on at least one occasion, with a knife and handgun.
After demanding cash, the suspects allegedly kicked and punched staff, then stole money, cigarettes, vaping products and lottery tickets.
The boys between the ages of 14 and 16 are facing robbery and weapons charges.
The 23-year-old man is facing a robbery charge and one count of conspiracy to commit an indictable offence.