Objectives: The aim of this study is to determine which type of vertical relationship (between molar apices and the sinus floor) is correlated with the most favorable bone to implant contact (BIC). Methods: The CBCT database of the Faculty of Dental Medicine was used for datasets. For each dataset, a prosthetically-driven virtual implant placement was placed in the remaining interradicular bone. Potential BIC was measured using two different implant macrogeometries (straight and tapered). Results: The study included 20 maxillary molars with divergent root anatomy: 90% of the molars had a type II vertical relationship with the sinus floor, while only 10% had type III. Mean pBIC surface for second molars was significantly higher for straight implants compared to tapered implants. However, no significant differences in BIC% means between straight and tapered implants for any of the comparisons was found. Conclusions: Implant macrogeometry was found to have an impact on achieving higher pBIC values in certain situations, such as for second molars and type II relationship with the sinus floor. The study highlights the need for incorporating 3D software analysis in pre-operative surgical planning.