Methods and systems for enhanced head-to-head hybrid gaming are provided. An enhanced head-to-head hybrid game has a gambling game with a real world engine that provides a randomly generated payout for the gambling game, an entertainment software engine that executes an entertainment game providing outcomes upon a player's execution of the entertainment game, and a game world engine that manages the entertainment software engine and communicates gameplay gambling event occurrences based upon a player's execution of the entertainment game that trigger the gambling game. A global betting manager receives player performance measurements from the game world engine, determines tournament eligibility, assigns a tournament handicap based at least in part upon the performance measurements from the game world engine and sends information concerning these parameters to the game world engine which is configured to implement each assigned handicap and tournament eligibility within the enhanced head-to-head hybrid game.