Police say the man was in the 300 block of Kennedy Street on Monday when the security guard denied him entry to a building. He then pulled out a gun and pointed it at the guard before trying to rob him.
The victim fled and notified police.
Officers spotted the man in the area of Kennedy Street and Ellice Avenue, where he pointed the handgun at police in their vehicle.
He was eventually located in the rear parking lot of Portage Place and taken into custody.
A replica handgun was located nearby.
Oliver Scott, 29, of Winnipeg has been charged with numerous offences.