Background: Stress urinary incontinence (SUI) is quite common in women, impairing the quality of life. Diabetes mellitus may exacerbate pelvic floor dysfunction and alter treatment response. Platelet-rich plasma (PRP) is a regenerative option to treat SUI; however, data in women with diabetes are limited. This prospective, non-randomized comparative cohort study evaluated PRP outcomes in diabetic versus non-diabetic women with SUI. Methods: Women with SUI (n = 102; non-diabetic n = 80, diabetic n = 22) received up to three PRP injections at 4–6-month intervals. They were evaluated using the Stamey scale before and after treatment, via the King’s Health Questionnaire (KHQ), assessed at baseline and after each session. Within-group change was tested using Friedman’s test with Dunn–Bonferroni post hoc comparisons; between-group differences used Mann–Whitney U tests. Results: PRP was associated with significant improvements across KHQ domains, with the largest gains by the second injection and smaller increments thereafter. Non-diabetic participants showed earlier, more uniform improvement and additional gains from post-PRP1 to post-PRP2/3. Diabetic participants improved later, with fewer between-session differences. Regarding the Stamey scores, our study concluded that diabetics and non-diabetics improve with PRP treatment, whereas the diabetics treated with insulin have not reached statistical significance in improving SUI. Conclusions: PRP was associated with meaningful, multi-domain improvement in women with SUI, with the most benefit by the second injection and continued reduction in symptom burden thereafter. Although patients with diabetes improved, they had higher total KHQ scores at baseline and later visits, supporting tailored counseling and potential protocol optimization for this subgroup.