Abstract: Shaft-mounted cup holders, hole-mounted cup holders, freestanding cup holders, and tabletop cup holders and methods of assembling and using the same. Shaft-mounted cup holders, hole-mounted cup holders, freestanding cup holders, and tabletop cup holders are based on a cup holder assembly that includes, for example, a 2-cup plate or a 4-cup plate in relation to a center fastener, wherein the 2-cup plate, the 4-cup plate, and the center fastener are designed to be slidably or permanently affixed to a shaft or pole, such as the shaft or pole of a table umbrella or beach umbrella or a stand-alone shaft or pole configured for use with the cup holders.