Brian Graham scored twice for Raith Rovers as they sailed comfortably into the next round of the Ramsdens Cup.
Allan Walker put the home side in front after seven minutes before Graham doubled their lead with a fine header on 32 minutes.
Pat Clarke made it three before Rovers stopper David McGurn was sent off for a foul in the area, with Paul Watson slotting home the penalty that followed.
The Fifers stretched their lead in the second half when Graham scored his second to make it 4-1.
Lloyd Young reduced the deficit for Montrose when he found the net after 77 minutes but Greg Spence had the final say with a fifth goal for Rovers in the 90th minute.
McGurn, Thomson, Ellis, Hill, Malowne, Grant Anderson (Callachan 59), Stuart Anderson, Walker, Hamill, Brian Graham (Greig Spence 85), Clarke (Laidlaw 44). Subs Not Used: Donaldson, Vaughan.
Grant Anderson, Hill. Goals: Walker 7, Brian Graham 32, Clarke 42, Brian Graham 54, Greig Spence 90.
Sandy Wood, McNalley, Cambell, Lunan, Watson, Grey, Masson, McLeish (Young 57), Johnston, Boyle, Gary Wood. Subs Not Used: Dean Easton, Crawford, Mosson, Gordon.
Watson 45 pen, Young 77.