Out of all the Scottish League Cup winning managers, Walter Smith, Jock Stein, and Scot Symon each won six, tying for the most wins.
Scot Symon, Jock Stein and Walter Smith are the most successful managers in the history of the competition, having each won 6 Scottish League Cups during their careers. 
Walter Smith (6) Jock Stein (6) Scot Symon (6) 
