A system and method are provided for implementing a uniquely automated, and otherwise gamified, version of a Squares Game. The disclosed schemes incorporate technology for hosting on, or interacting/reacting with, potential participants' mobile and personal communicating and computing devices. The disclosed schemes simplify hosting of, and participation in, a unique implementation of a Squares Game associated with one or more live event, including but not limited to live sporting events. The disclosed schemes introduce a streamlined process for registering participants, selecting interior game squares, among many players, and executing all of the gaming functions in an automated manner to include identification and notification of winners when their winning numbers are determined to be associated with respective numbers in the live event.