Simple Summary: Oral squamous cell carcinoma is the most common oral carcinoma worldwide. Despite medical improvements and applied research, the 5-year- overall survival rate amounts to ca 51 percent. Early recurrence diagnosis is a key driver for increasing the cure rate which underlines the importance of this study. The study aims to show how surveillance imaging of OSCC patients might be influenced by factors such as radiotherapy treatment, contrast enhancement, and the type of imaging (CT, NMRI). Further analysis is needed to determine if there is any difference between patients showing clinical and radiological patterns or only radiological patterns and if there is any connection between the histopathological result and those influence factors to improve the value of surveillance imaging in follow-up treatment and thus the cure rate. The evaluation of surveillance imaging of OSCC patients is a difficult task physicians have to face daily. Multiple patients experience a recurrence of this disease, which underlines the importance of regular patient monitoring programs. Our study analysed the value of surveillance imaging, such as computed tomography (CT) and nuclear magnetic resonance imaging (NMRI), as a patient monitoring programme and its effectiveness in achieving improvement in early recurrence detection. The study comprised 125 patients, out of which 56 (n = 56) showed radiological and 69 (n = 69) showed clinical and radiological conspicuous patterns in domestic follow-ups, respectively. The use of CT and NMRI showed a significant dependence on the histological result (p = 0.03). However, the different groups showed no significant dependence on the histological result (p = 0.96). The distribution of the histological biopsies, which were taken due to radiological changes, were prone to wrong positive diagnoses (false positives) in 71 percent. To conclude, imaging modalities should be chosen for each patient individually to reduce false positives, improve the early detection of recurrence, and increase the cure rate. [ABSTRACT FROM AUTHOR]