The aim of this study was to evaluate the influence of a calcium silicate-based sealer (iRoot SP), with or without a core material, on bond strength to radicular dentin, in comparison with various contemporary root filling systems. Root canals of freshly extracted single-rooted teeth (n = 60) were instrumented using rotary instruments. The roots were randomly assigned to one of the following experimental groups: (1) a calcium silicate-based sealer without a core material (bulk-fill); (2) a calcium silicate-based sealer + gutta-percha; (3) a calcium silicate-based sealer + Resilon; (4) a methacrylate resin-based sealer (Real Seal SE) + Resilon; (5) an epoxy resin-based sealer (AH Plus) + gutta-percha, and (6) a mineral trioxide aggregate-based endodontic sealer (MTA Fillapex) + gutta-percha. Four 1-mm-thick sections were obtained from the coronal aspect of each root (n = 40 slices/group). Push-out bond strength testing was performed at a cross-head speed of 1 mm/min, and the bond strength data were analyzed statistically by one-way analysis of variance and Tukey tests (p < 0.05). The highest and lowest debonding values were obtained for the calcium silicate-based sealer bulk-fill and mineral trioxide aggregate-based endodontic sealer + gutta-percha groups, respectively (p < 0.05). It was concluded that the calcium silicate-based sealer showed higher resistance to dislocation in the bulk-filled form than in conjunction with the tested core filling materials. When the calcium silicate-based sealer was placed in bulk, its dislocation resistance was similar to that of commonly used sealer + core root filling systems. Thus, the concept of using a calcium silicate-based sealer in bulk can be more easily advocated in clinical practice.