Introduction: Prognostic evaluation of Oral Squamous Cell Carcinoma (OSCC) is mainly based on [Tumour (T), Nodes (N), and Metastases ( M)] staging. To predict the biological and clinical behaviour of a tumour, histological grading systems plays an important role. Modified Anneroth's grading system includes three parameters each for histologic features and tumour-host relationship. Aim: To compare and analyse the histological features of tumour center and periphery of non metastatic and metastatic OSCC according to Anneroth's histopathological classification and its association with regional lymph node metastasis. Materials and Methods: A retrospective pilot study was conducted on 20 histopathologically proven cases of OSCC collected from the Department of Oral Pathology and Oral Microbiology, Vinayaka Mission's Sankarachariyar Dental College, Salem, Tamil Nadu, India. The OSCC cases that reported from March 2018 to June 2020 were included in the study. Among 20 cases, 10 non metastatic and 10 metastatic cases, were retrieved from archival blocks. Scores for the morphology and tumour-host relationship of non metastatic and metastatic tumours was assessed and graded by Anneroth's grading system; then compared with the Broders histopathological grading system. The histopathological scoring of lymph node was based on TNM staging. Chi-square test and Spearman's correlation coefficient analysis was done. Results: Anneroth's grading system showed a significant difference in pattern of invasion in tumour periphery of metastatic OSCC (p-value=0.01). Compared to Broder's, Anneroth's classification showed a highly significant corelation with lymph node metastasis (p-value=0.001). Conclusion: Hence, Anneroth's histopathological grading system can be used to predict the biological changes in metastatic and non metastatic OSCC and its increased possibility of regional lymph node metastasis.