In the present retrospective study, we aimed to assess the replicability and reproducibility of a novel digital measurement technique for analyzing the volumes of the left and right maxillary sinuses and the nasal and maxillary sinus airway complex after a sinus lift procedure using the lateral window approach, to provide an accurate measurement technique for easily applying in clinical practice and to allow pre-operative assessment of maxillary sinus lift surgery, avoiding complications and making surgery more predictable. Material and Methods: Thirty patients with partially edentulous posterior maxilla were selected and submitted to bilateral sinus lift using the lateral window approach technique, with grafting materials selected and submitted to cone beam computed tomography (CBCT) scans, both pre- and postoperatively. Then, datasets were uploaded to therapeutic digital planning software to measure the volume of the right and left maxillary sinuses and the nasal and maxillary sinus airway complex. Gage R&R statistical analysis was performed to assess the replicability and reproducibility of the digital measurement technique. Results: The variability attributable to the novel digital measurement technique was 3.4% for replicability and 3.4% for reproducibility of the total variability of the samples. Conclusion: The novel digital method proposed is a replicable and reproducible technique for analyzing the volume of the right and left maxillary sinuses and the nasal and maxillary sinus airway complex after a sinus lift using the lateral window approach technique, allowing an accurate pre-operative assessment of maxillary sinus lift surgery, avoiding complications and making surgery more predictable.