An insertion unit can be provided to save labor required for a cloth insertion operation. In addition, provided is a cloth insertion device including the insertion unit and an intermediate device. The insertion unit includes a lower section on which one side of a cloth is placed and that transports the cloth upward, and an upper section that is disposed above the lower section and that transports the cloth upward. The lower section includes a placement section on which the cloth is placed, the upper section includes a movable section that is rotatable upward and downward at a position above the placement section, the movable section having rotated upward rotates downward when the one side of the cloth is placed on the placement section, and the one side of the cloth is transported upward with the one side being sandwiched between the placement section and the movable section.