The objective of this study was to analyze the outcome of first-time surgical closures of oroantral communications (OAC) after tooth extractions. Using a billing software, all patients treated in a surgery department were filtered for interventions of the maxillary sinus indicative of OAC therapy. Out of 221 initially eligible cases, the charts of 162 cases fulfilling the inclusion criteria were retrospectively evaluated for the outcome in terms of symptom-free OAC closure as well as possibly influencing patient and treatment factors. The analyzed cohort included 98 males (60.5%) and 64 females (39.5%) with a mean age of 48.6 years (range 17 to 86 years). The maxillary 1st molar (38.3%) was the most common site requiring OAC closure. In 60.5% of the cases, surgical OAC closure was performed immediately after tooth extraction. The Rehrmann flap (72.2%) was the most frequently used technique for surgical OAC closure. 94.4% of surgical OAC closures were successful. Gender and age did not influence the outcome. In contrast, the site of OAC and the time interval from tooth extraction to OAC closure affected the results. Furthermore, the Rehrmann flap, alone or in combination with biomaterials, was superior to the mere suturing (with or without biomaterials) of the OAC site. In conclusion, the Rehrmann flap alone or in combination with biomaterials provided high success rates for first-time surgical OAC closure. With regard to the study parameters, an OAC in the 3rd molar area and an extended interval from tooth extraction to OAC closure negatively influenced the resolution of OAC. However, results must be interpreted cautiously considering the retrospective study design and the limited number of cases.