Purpose: To comparatively evaluate transcrestal sinus floor elevation (tSFE) and lateral sinus floor elevation (lSFE) at sites with different residual bone heights (RBHs). Materials and Methods: A re-analysis of data from a parallel-arm, randomized trial comparatively evaluating tSFE and lSFE was performed. Within each RBH interval (< 4 mm or ≥ 4 mm), tSFE and lSFE groups were compared for chair time, surgery-related costs, morbidity, and radiographic parameters (including the proportion of the implant surface in direct contact with the radiopaque area [totCON%]). Results: The intention-to-treat (ITT) population consisted of 29 and 28 patients in the tSFE and lSFE groups, respectively. Irrespective of RBH, both tSFE and lSFE lead to a median totCON% of 100%. At sites with RBH < 4 mm, pain severity was significantly higher at days 0 and 1 in the tSFE group, with no intergroup difference in the dose of analgesics. LSFE was associated with a significantly higher frequency of bruising and greater cost. At sites with RBH ≥ 4 mm, a significantly lower frequency of postoperative signs/symptoms, less chair time, and lower costs were observed in the tSFE group. Conclusions: The selection of tSFE or lSFE within the investigated RBH intervals seems to be supported by differences in chair time, costs, and morbidity between the two techniques. At sites with RBH < 4 mm, clinicians preferring tSFE should encourage the administration of analgesics according to a predefined plan in the early postoperative phase. At sites with RBH ≥ 4 mm, tSFE should be preferred to lSFE due to reduced chair time, costs, and morbidity.