The aim of the present systematic review was to investigate the effect of residual bone height (RBH) and vertical bone gain on new bone formation (NBF) and graft shrinkage after lateral sinus lifts using different biomaterials. Methods: An electronic search was conducted on three databases to identify randomized controlled trials (RCTs) published until January 2021 with at least one follow-up at 6 months and at least five patients treated, comparing biomaterials used for maxillary sinus augmentation with a lateral approach. Graft volumetric changes, RBH, vertical bone gain, implant failure, and post-operative complications were evaluated. The risk of bias was assessed using the Cochrane tool. Results: We used 4010 identified studies, of which 21 were RCTs. Overall, 412 patients and 533 sinuses were evaluated. Only three publications had an overall low risk of bias. After 6 months, xenograft (XG) showed the least volume reduction (7.30 ± 15.49%), while autogenous graft (AU) was the most reabsorbed (41.71 ± 12.63%). NBF appeared to not be directly correlated with RBH; on the contrary, the overall linear regression analysis showed that NBF significantly decreased by 1.6% for each mm of postoperative vertical graft gain. This finding suggests that the greater the augmentation, the lower the NBF. A similar tendency, with a regression coefficient even higher than the overall one, was also observed with alloplast (AP) and XG. Conclusions: The present results suggested that NBF was essentially independent of preoperative bone height. On the contrary, the smaller the volume was of the graft placed, the higher the amount of new bone formed, and the smaller the graft shrinkage was. Minimizing the augmentation volume might be beneficial to graft healing and stability especially when using AP and XG.