Based on the popular NHK anime & manga created by CLAMP, Itsumo Sakura-chan to Issho (Always with Sakura-chan) is a game which makes use of a real-time clock feature to provide variations in gameplay based on the time of day. The player is tasked with utilizing the clock feature to help Sakura locate the Clow Cards, from the perspective of her guide, Cerberus. The player explores various rooms at various times of day in order to find the cards, while also partaking in Sakura's time at school.

Players can utilize a Game Boy Printer to print out themed stickers, including various characters, icons, and whatever text the player enters. Various mini-games are also available.