Purpose: To determine effect of upper eyelid surgery on headache symptoms. Methods: Consecutive adults undergoing upper eyelid surgery for obscuration of superior visual field, who also reported headache symptoms for greater than 1 year completed a pre- and postoperative Headache Impact Test-6 quality of life questionnaire (study group). A cohort of patients undergoing other oculoplastic procedures with headaches also completed the questionnaire pre- and postoperatively (control group). The study was conducted over a 2-year period. Neither the patients nor the study investigators were masked. Results: Twenty-eight patients met criteria for the study group, and 19 patients in the control group. Mean age was 58.7 and 60.7 years, respectively. There was no statistically significant difference in preoperative location of headaches. There was no significant difference in mean Headache Impact Test-6 scores preoperatively, 57.7 study group, 58.1 control group, p = 0.86. Mean postoperative scores were lower (improved) in the study arm, 45.3, as compared with the control arm, 58.6, p < 0.05. There was no statistically significant difference between individual preoperative survey questions between the study arm and control group, while every Headache Impact Test-6 question significantly improved in the study arm compared with the control arm. Mean Headache Impact Test-6 score improved 12.4 points in the study arm after surgery (p < 0.05), while the mean postoperative score worsened by 5 points in the control arm, but this was not significant (p = 0.48). Subjectively, 25 of 28 study patients, and 4 of 19 control patients noticed at least some improvement in headache symptoms after surgery. Conclusions: Correction of visually significant upper eyelid position may improve chronic headache symptoms.