Background: Dysmenorrhea is a menstrual condition characterized by severe and frequent pain related to menstruation. Primary dysmenorrhea is a major problem worldwide since its prevalence ranges from 28% to 94% in some populations. Studies in specific populations of changes in the prevalence of dysmenorrhea over time have been scarce. Therefore, the aim of the present study was to compare the prevalence and characteristics of primary dysmenorrhea between two independent populations of Mexican university women over time (2010 versus 2020). Methods: An anonymous multiple-choice questionnaire was completed by two independent groups of students. Variables from the two studies were extracted and compared between them. The degree of dysmenorrheic pain was assessed by a 100 mm visual analog scale (VAS) ranging from “no pain” to “the worst pain imaginable”. Study A included 1539 women (published in 2010), and Study B included 2154 women (realized in 2020). Results: A total of 3693 students were surveyed. Dysmenorrhea prevalence was established in 62.4% (n = 961) in survey A and 78.9% (n = 1699) in survey B (p 0.05). The pain means were 54.1 \pm 23.4 mm and 64.0 \pm 20.6 mm for Studies A and B, respectively (p 0.05). Moderate-severe pain was reported by 753 (78.4%) women in Study A and 1546 (91.0%) women in Study B. Significantly more students from Study B (90.4%) had limitations in daily activities due to dysmenorrhea compared to women from Study A (65.0%) (p 0.05). School absenteeism in Study B (50.6%) was significantly higher than that in Study A (27.4%) (p 0.05). Conclusions: The prevalence of primary dysmenorrhea and the presence of symptoms in students showed statistically significant increases over time (2010 versus 2020). Similarly, due to the symptoms of dysmenorrhea, school absenteeism increased significantly, and daily activities were progressively affected.