Background/Objectives: Pelvic floor dysfunction (PFD) encompasses urinary incontinence (UI), anorectal disorders (ARDs), and other related conditions that frequently coexist. Evidence on the prevalence and determinants of ARD among patients with UI, particularly in Middle Eastern populations, remains limited. This study aimed to assess the prevalence of ARD in UI patients and identify key clinical and demographic factors associated with anorectal disorders. Methods: A retrospective cohort study was conducted between January 2017 and June 2025. Consecutive adult patients diagnosed with UI were included. Demographic, clinical, obstetric, and surgical characteristics were extracted from medical records. Categorical comparisons were performed using chi-square and Fisher’s exact tests, while predictors of ARD were analyzed using multivariable logistic regression. Results: Among 494 patients with UI, ARD was present in 115 cases, yielding a prevalence of 23.3%. The most frequent ARD diagnoses were hemorrhoids (29.8%), obstructive defecation syndrome (19.3%), and fecal incontinence (18.1%). Patients with ARD more often had stress UI (25.2% vs. 18.5%) and overflow UI (4.3% vs. 2.1%) compared with those without ARD. Chronic constipation was significantly associated with ARD (39.7% vs. 10.7%, p < 0.001), as were hypothyroidism (31.8% vs. 21.4%, p = 0.037), psychological conditions (37.1% vs. 21.0%, p = 0.003), and sexual dysfunction (64.7% vs. 19.0%, p < 0.001). Logistic regression identified rectocele (aOR = 6.54, 95% CI: 3.18–13.45, p < 0.001) and previous pelvic surgery (aOR = 2.27, 95% CI: 1.17–4.41, p = 0.016) as independently associated with ARD. Increasing age was inversely associated with ARD (aOR = 0.98, 95% CI: 0.96–0.99, p = 0.014). Conclusions: Our findings underscore the need to incorporate anorectal and sexual health screening in UI patients. Early recognition, coupled with multidisciplinary team-based management, may help optimize outcomes, enhance treatment compliance, improve quality of life, and reduce the long-term burden associated with PFD.