Handheld video gaming has been a staple in the video game industry for over thirty years. While the current generation of handheld video game consoles are much more powerful than their predecessors, a substantial community of enthusiasts still enjoy the tactile feel and retro aesthetics of much older and more traditional hardware and media. Newer handheld devices that aim to replicate this through software emulation and contemporary hardware typically lack the wireless multiplayer connectivity that has since become a key feature for modern day handheld and mobile video game titles and devices. In this paper, we analyze these technologies and their software by developing our own basic handheld gaming console with wireless multiplayer capabilities for cooperative and competitive gaming between devices through the use of Wi-Fi ESP8266 based microcontrollers. The results demonstrate the development of two separate nodes capable of complete wireless interconnectivity for simultaneously running a proof of concept multiplayer recreation of the classic “Pong” arcade game.