Controlling the gelatinization of starch is vital for achieving desired food design, and sugars and oligosaccharides (OSs) have a significant impact on the gelatinization temperature (Tgel) of starch. This study delved into the effects of sucrose, maltotetraitol, and ten glucose-based OSs with different glycosidic linkage patterns, degrees of polymerization (DP), and linear or cyclic structures on the Tgel of wheat starch. The objective of this study was to uncover the underlying mechanisms by which OSs alter Tgel to support the design and use of OSs for sugar reduction in baked goods. Findings underscore the notable impact of both OS concentration and type on Tgel. Increases in OS concentration resulted in Tgel elevation, closely linked to changes in water activity and effective water volume fraction (φw,eff). Among the same DP OSs, a higher effective number of hydroxyl groups available for hydrogen bonding per unit volume of the solute (NOH,S/Vs) corresponded to increased Tgel, indicating higher hydroxyl density in OSs leads to an increased number of hydrogen bond formation between OSs and starch that stabilizes the structure. Of particular note is that isomaltose (α-1,6 linkage) significantly elevated the Tgel more than the other DP2 OSs, trehalose (α-1,1 linkage), kojibiose (α-1,2 linkage), and maltose (α-1,4 linkage), even with low NOH,S/Vs. This underscores the importance of OS structural flexibility in antiplasticizing starch. The study enriches our understanding of how OSs influence starch Tgel relative to the effects of sucrose, emphasizing the roles of intermolecular hydrogen bonding and OS structural flexibility in elevating starch Tgel in a manner which is beneficial for maintaining the texture and structural properties of reduced-sugar baked goods.