As digital display devices become more and more indispensable, associated health problems have started to increase. We aimed to investigate the frequency and relationship of digital display device usage behaviours and dry eye syndrome (DES) in medical students. An observational, cross-sectional study was conducted on medical school students who voluntarily participated in our study online, about the duration and variety of their digital screen use, usage patterns, and protective measures, together with the Ocular Surface Disease Index (OSDI) questionnaire. Where necessary, the Schirmer-I, tear break-up time, and fluorescein staining tests were carried out. Of the 255 participants, 75.3% (n = 192) were female, 63.1% (n = 161) had no refractive vision defects, and 45.9% used smartphones for more than 5 h a day. According to the OSDI scores for DES screening, only 36.1% of the participants were normal, 17.3% had mild DES, 20.4% had moderate DES, and 26.3% had severe DES. A positive correlation was found between digital display usage time in hours per day and a high OSDI score. As the distance between the eye and the screen decreased, the DES score increased, which is significant for computer, e-book, and tablet use (P < 0.005). The DES rate of the 25 participants who underwent further evaluation was 40% for the tear break-up time test and 52% for the fluorescein staining test. The high prevalence of DES due to digital screen use among medical school students highlights the importance of DES screening as a preventive measure in family medicine.