The NiTi alloy can be trained by repetitive loading or heating cycles. As a result of the training, a two-way shape memory effect (TWSME) can be induced. Considerable research has been reported regarding the TWSME trained by tensile loading. However, the TWSME trained by compressive loading has not been investigated nearly as much. In this paper, the TWSME is induced by compressive loading cycles and the two-way shape memory strain is evaluated by using two types of specimen: a solid cylinder type and a tube type. The TWSME trained by compressive loading is different from that trained by tensile loading owing to the severe tension/compression asymmetry as described in previous research. After repetitive compressive loading cycles, strain variation upon cooling is observed, and this result proves that the TWSME is induced by compressive loading cycles. By performing compressive loading cycles, plastic deformation in NiTi alloy occurs more than for tensile loading cycles, which brings about the appearance of TWSME. It can be said that the TWSME is induced by compressive loading cycles more easily. The two-way shape memory strain increases linearly as the maximum strain of compressive loading cycles increases, regardless of the shape and the size of the NiTi alloy; this two-way shape memory strain then shows a tendency towards saturation after some repeated cycles.