Various techniques are disclosed for facilitating side wagering activities conducted at a casino which includes a casino gaming network. In at least one embodiment, the gaming network includes a plurality of gaming devices, including a first gaming device. A side wager request may be received for placing a first side wager relating to a first target. In at least one embodiment, the first target may be selected from a group of possible targets which, for example, may include, but are not limited to one or more of the following (or combination thereof): casino players, game tables, electronic gaming devices (EGDs), game themes, game denominations, game paytables, etc. An identity of a first player associated with generating the first side wager request may be determined. A first side wager session may be automatically initiated.