For frontal sinus inverted papilloma (FSIP) management, an endoscopic endonasal approach (EEA) can be combined (or not) with an external approach by an osteoplastic flap (OPF) or with a more conservative open approach. The present study aims to describe our experience in the management of FSIP, focusing on disease-related and anatomical features influencing outcomes and recurrence. This case series of FSIP investigated anatomical and disease-related predictors of recurrence associated with EEA or a combined EEA-OPF approach. A systematic review was also performed, selecting publications on IP with the insertion point in the frontal sinus or frontal recess. Among 30 patients included, 18 underwent EEA, while 12 received a combined EEA-OPF approach. During a median follow-up of 37 months, the frontal sinus was cleared of IP in all cases except 2 in the EEA group, who presented a complex posterior wall shape of the frontal sinus. From the systematic review, a combined EEA-OPF approach was associated with a lower risk of recurrence. A correct indication for a combined EEA-OPF approach is paramount and should integrate all disease-related and anatomical features, including posterior wall shape.