Rheumatoid arthritis (RA) commonly causes inflammation in the joints and periarticular structures. The association between RA and rotator cuff (RC) has been reported; however, epidemiological studies on RA and RC tendons are scant. Therefore, we investigated RC disease (RCD) risk and analyzed the effects of RA medication, steroids, and methotrexate, on the risk of RCD for patients with RA. We conducted a retrospective cohort study with a 6-year longitudinal follow-up in Taiwan. Patients who received RA diagnoses between 2004 and 2008 were enrolled in the study cohort. The non-RA control cohort comprised age- and sex-matched controls. Propensity score matching was used for other comorbidities and treatments. The hazard ratios (HRs) and adjusted HRs (aHRs) were estimated after confounders were adjusted for. Effects of steroid and methotrexate use on RCD risk were also analyzed. We enrolled 4521 RA patients (study cohort) and 22,605 matched controls. RCD incidence was 145 and 91 per 100,000 person-years in the RA and control cohorts, respectively. In the RA cohort, the crude HR for RCD was 1.62 (95% confidence interval (CI), 1.41⁻1.86, p < 0.001), and the aHR was 1.56 (95% CI, 1.36⁻1.79, p < 0.001). The methotrexate nonusers exhibited an aHR (vs. controls) of 1.61 (95% CI, 1.40⁻1.85, p < 0.001), but the methotrexate users did not have a significantly higher aHR than the controls. The steroid nonusers had an aHR (vs. controls) of 1.69 (95% CI, 1.46⁻1.96, p < 0.001), but the aHR of the steroid users was not significantly higher than the control aHR. Patients with RA had a higher risk for RCD compared with the non-RA control cohort. Steroids or methotrexate use significantly reduces the risk of RCD occurrence in patients with RA. Treatment for RCD symptoms and controlling inflammatory process are important to ensure high-quality care for patients with RA.