Toronto police say the two victims were approached in the early hours of Sunday morning, as they walked along Jones Avenue, near Dagmar Avenue.
It is alleged that the victims were approached by a group of males who demanded they hand over their money.
Const. Jenniferjit Sidhu told CBC News that one of the suspects is alleged to have pointed to a gun on his waistband when making the demand.
The men refused and police say they were both assaulted.
Sidhu said that one man was punched in the back of the head, while the other was tripped and then beaten and kicked.
The suspects fled the scene.
Sidhu said the victims called police and arrests soon followed. A gun was seized.
Two 18-year-old men and four youths, aged 15 to 17, now face charges of robbery with a firearm, using a disguise with an intent to commit an indictable offence and possession of property obtained by crime under $5,000.
The six accused were scheduled to appear in court on Monday.
Police believe there may be more victims.
Anyone with information is asked to contact investigators at 416-808-5500. Tips can also be passed on anonymously through Crime Stoppers at 416-222-8477.