Virtual competitive group management systems and methods are provided herein. Exemplary systems may execute methods via one or more processors, which are programmed to compare one or more skill levels of a player to skill levels of a plurality of competitors, wherein a skill level is associated with player competitiveness within the interactive game, determine at least one of the plurality of competitors who have at least one skill level that is greater than the skill level of the player, and place the player and the at least one of the plurality of competitors into a competitive group such that the player is at a competitive disadvantage to at least one of the plurality of competitors.