Methods and apparatus for facilitating and monitoring player financial and player tracking/reward transactions, including the tracking of player losses, are disclosed. In one embodiment, a system includes at least one server and a plurality of gaming machines and/or a game generator for transmitting game information to a remote game play location. The server has a memory containing data files corresponding to players. The data files contain information such as credits or monies in an account which belong to the player and which may be used by the player to play games. The data files also contain player tracking information, such as points awarded to a player based upon their game play and/or information regarding player expenditures or deductions, such as amounts wagered by a player. In one embodiment, a player and a casino may manage the player's accounts, such as by placing criteria upon the account(s), tracking a player's gain or loss while playing games, awarding awards such as prizes and credits for free game play or redeemable awards.