Background/Objectives: To explore potential dry eye-related ocular surface functional alterations in women at the time of first diagnosis of endometriosis or adenomyosis in a real-world clinical setting. Methods: This was a cross-sectional case–control study. Patients were evaluated at the time of initial diagnosis, prior to initiation of any hormonal therapy, to reflect real-world clinical conditions. Participants underwent a standardized ocular surface assessment comprising the Ocular Surface Disease Index (OSDI) questionnaire, Schirmer test, and multimodal TearCheck^® analysis, including Non-Invasive Break-Up Time (NIBUT), Tear Film Stability Evaluation (TFSE), Meibography, and Abortive Blinking^®. Results: A total of 71 women were included: 41 with endometriosis or adenomyosis and 30 without known gynecological disease. Patients reported significantly higher OSDI scores than controls (p < 0.05). Objective testing demonstrated lower Schirmer values, reduced tear film stability, and more pronounced Meibomian gland dropout in the patient group (all p < 0.05). Differences were consistently observed across both subjective and objective parameters. Conclusions: Women with endometriosis and/or adenomyosis exhibited significantly altered ocular surface parameters compared with women without known gynecological disease. These findings suggest a possible association between gynecological disease and ocular surface dysfunction. Greater awareness of potential ocular involvement may encourage closer collaboration between gynecology and ophthalmology in the care of affected patients.