Olefin block copolymer (OBC), with its low hard segments, can form unique space-filling spherulites other than confined-crystallization morphologies, mainly due to its weak phase-separation. In this work, 1,3;2,4-Bis(3,4-dimethylbenzylidene) sorbitol (DMDBS), a well-known nucleating agent, was used to tailor the crystallization behavior and crystalline morphology of OBC. It was found that DMDBS can precipitate within an OBC matrix and self-assemble into crystalline fibrils when cooling from the melt. A non-isothermal crystallization process exhibited an increased crystallization rate and strong composition dependence. During the isothermal crystallization process, DMDBS showed a more obvious nucleating efficiency at a higher crystallization temperature. OBC showed typical spherulites when DMDBS was added. Moreover, a low addition of DMDBS significantly decreased the crystal size, while a large addition of DMDBS induced aggregates, due to the limited miscibility of DMDBS with OBC. The efficient nucleating effect of DMDBS on OBC led to an increased optical transparency for OBC/DMDBS composites.