Osteoarthritis (OA) is a highly prevalent chronic joint disorder affecting ~600 million individuals worldwide and is characterized by complex pain mechanisms that significantly impair patient quality of life. Challenges exist in accurately assessing and measuring pain in OA due to variations in pain perception among individuals and the heterogeneous nature of the disease. Conventional pain assessment methods, such as patient-reported outcome measures and clinical evaluations, often fail to fully capture the heterogeneity of pain experiences among individuals with OA. This review will summarize and evaluate current methods of pain assessment in OA and highlight future directions for standardized pain assessment. We discuss the role of animal models in enhancing our understanding of OA pain pathophysiology and highlight the necessity of translational research to advance pain assessment strategies. Key challenges explored include identifying phenotypes of pain susceptibility, integrating biomarkers into clinical practice, and adopting personalized pain management approaches through the incorporation of multi-modal data and multilevel analysis. We underscore the imperative for continued innovation in pain assessment and management to improve outcomes for patients with OA.