Knowledge of the anatomical relationships between the maxillary sinus (MS) and posterior teeth is important to prevent complications when endodontic or oral surgical procedures are performed. The aim of this study was to evaluate the relationships between the root apices of maxillary posterior teeth and the MS floor. Three oral radiologists evaluated 851 posterior teeth (1969 roots) imaged with cone beam computed tomography. The roots were analyzed individually in parasagittal sections, on which the most superior point of the apex was observed. A qualitative evaluation was performed, and each root was assigned a proximity score: 1, root invaginating the MS; 2, root in close contact with the MS floor; 3, root with no relationship with the MS; and 4, root with a measurable proximity to the MS. For roots classified as score 4, the distance to the MS floor was measured (quantitative analysis). Student t tests, 1-way analysis of variance, and simple linear regression analysis were performed (P < 0.05). The qualitative analysis revealed that the mesiobuccal root of the second molar had a pronounced proximity to the MS. The quantitative analysis revealed no differences in distance to the MS between right and left posterior teeth or between the different roots of the same tooth. In relation to the MS, the second molar was positioned closest, followed by the first molar, second premolar, and first premolar. Except for the comparison between mean distances of the second premolar and first molar (P = 0.11), the differences between groups of teeth were statistically significant (P < 0.05). Simple linear regression analysis showed that the more posterior the tooth was in relation to the midline, the shorter the mean distance from the root apex to the MS floor (P < 0.05). The mesiobuccal roots of second molars were closest to the MS. Second molars exhibited the shortest distances between their root apices and the MS and the greatest number of roots that were invaginating or in close contact with the MS. Therefore, second molars require special attention when endodontic or oral surgical approaches involve those regions.