Background: Diabetes and obesity are established risk factors for stroke. The current study aimed to assess risk factors of ischemic stroke recurrence in diabetic patients based on their body mass index (BMI). Methods: A total of 4005 diabetic patients who had a history of ischemic stroke were identified in a retrospective cross-sectional dataset from the Malaysian National Neurology Registry. Patients were classified based on BMI, and multivariable regression analysis was used to evaluate the association between risk factors and recurrent ischemic stroke. Results: Among obese patients, those with ischemic heart disease (aOR, 1.873; 95% CI, 1.131–3.103), received formal education (aOR, 2.236; 95% CI, 1.306–3.830), and received anti-diabetic medication (aOR, 1.788; 95% CI, 1.180–2.708) had a higher stroke recurrence risk, while receiving angiotensin receptors blockers (aOR, 0.261; 95% CI, 0.126–0.543) lowered the odds of recurrence. Overweight patients with hypertension (aOR, 1.011; 95% CI, 1.002–1.019) for over 10 years (aOR, 3.385; 95% CI, 1.088–10.532) and diabetes prior to the first stroke (aOR, 1.823; 95% CI, 1.020–3.259) as well as those received formal education (aOR, 2.403; 95% CI, 1.126–5.129) had higher odds of stroke recurrence, while receiving angiotensin-converting enzyme inhibitors (aOR, 0.244; 95% CI, 0.111–0.538) lowered the recurrence risk. Normal weight East Malaysians (aOR, 0.351; 95% CI, 0.164–0.750) receiving beta-blockers (aOR, 0.410; 95% CI, 0.174–0.966) had lower odds of stroke recurrence. Conclusions: Ischemic heart disease, hypertension, receiving anti-hypertensive agents, and educational level were independent predictors of recurrent stroke in obese patients. Managing the modifiable risk factors can decrease the odds of stroke recurrence.