Approaches to the C—H functionalization are of great importance in modern organic synthesis. Among their diversity, reactions of the hydride transfer (HT) are especially effective. The major research efforts are focused on cascade of 1,5-HT/6-endo-cyclization reactions. Over the recent 20 or 30 years, alternative reaction pathways leading after the HT step to five-, seven-, eight-membered, and other cycles or non-cyclic products have been developed. The hydride transfer has become an independent tool for the multi-vector C—H functionalization. In this review, we attempted classifying approaches to the alternative reaction pathways triggered by the HT step, as well as to cover new achievements in this area.