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Background. In Sudan, patients with oral squamous cell carcinoma (OSCC) presented lately in advanced stages. Surgical site infection (SSI) is one of the most common complications of surgical treatment of OSCC which significantly affects the clinical outcomes. The present study aimed to assess the frequency and risk factors of postoperative surgical site infection among OSCC patients underwent surgery at Khartoum Teaching Dental Hospital (KTDH). Methods. This is a prospective, analytical, hospital-based study conducted at KTDH during the period from 2022 to 2023. Patients with OSCC were surgically treated and assessed carefully for the development of the SSI. Results. Sixty patients were enrolled in the present study. Twenty-nine (48.3%) patients were above 61 years, with the predominance of males with 42 (70%) patients. The most involved site of OSCC was the lower gingivolabial region in 35 (39.3%) patients. Forty-seven (78%) patients were in advanced stages III and IV. Forty-five (80%) patients had modified radical neck dissection. Blood transfusion was administered in 50 (83.3%) patients. Twenty-six (43.4%) patients developed SSI; 15 (57.7%) patients of them were Toombak dippers. Development of SSI was found to be significantly associated with the tumour site (P value 0.9), clinical stage (P value 0.6), the number of transfused blood units (P value 0.04), and the duration of hospital stay (P value 0.04). In contrast, use of sutures for wound closure was associated with a reduced risk of developing SSI (P value 0.005). Conclusion. Surgical site infection was found in 43.4% of the OSCC patients. It was associated with advanced clinical stage and tumour site. Minimizing the number of blood units transfused intraoperatively, we decrease the duration of hospital stay and the use of sutures for wound closure decreases the risk of SSI significantly.