Background: In the later stages of a paramedian forehead flap (PMFF) surgery, the supratrochlear (STN) and branches of the supraorbital nerve (SON) are transected during flap inset above the supraorbital rim. This can lead to either a nerve release if the compression point was previously distal to the transection point or a new nerve compression through neuroma or scar tissue formation. We inferred that PMFF could be a model for understanding the correlation between STN/SON pathology and migraines headaches (MH). We hypothesized that patients undergoing PMFF would experience either a change in severity or an onset of a new headache (HA) or MH. Methods: One hundred ninety-nine patients who underwent a PMFF at a tertiary medical centre were identified and contacted by phone. Patients were asked about the presence of MH or HA before and after the procedure. If a patient reported a perioperative history of MH/HA, their pre- and postoperative MH/HA characteristics were recorded. Results: Of the 199 patients contacted, 74 reported no perioperative HA/MH history and 14 reported a perioperative history of HA/MH. Of these 14 patients, 5 had stable HA/MH pre- and post-surgery, and 9 reported a change in HA/MH post-surgery. In this subset of 9 patients, 3 reported change in HA/MH quality post-surgery, 1 reported HA/MH resolution post-surgery, and 5 reported new onset HA/MH post-surgery. Conclusion: Sixty-four percent of patients with perioperative HA/MH experienced a change in headache quality following surgery. These results suggest a potential connection between SON and STN pathology and HA/MH pathophysiology; further work is warranted.