Introduction: Spontaneous insufficiency fractures of the knee (SIFK) are stress fractures occurring in weight-bearing joints, particularly the knee, due to underlying conditions like osteoporosis. These fractures typically affect elderly, postmenopausal women, individuals with obesity, or those with osteoporosis. Additional risk factors include diseases affecting collagen formation and systemic conditions like systemic lupus erythematosus and prolonged corticosteroid use. The medial femoral condyle is the most affected site, and patients frequently present with acute knee pain without any significant trauma. MRI plays a crucial role in diagnosing these fractures. Materials and Methods: This retrospective review of knee MRI reports from January 2013 to January 2020 was conducted in a tertiary care centre, included 85 cases of SIFK and 85 age and gender matched controls. The analysis included insufficiency fractures of the knee joint and assessment of the associated pathologies like meniscal tears, ACL degeneration and osteoarthritis. The Radiological findings were analyzed using SPSS v27 to evaluate the spectrum of findings. Results: Majority of the study population (59.4%) were females, with the medial femoral condyle being the most frequently affected site. Partial-thickness cartilage loss was the most common finding in both femoral and tibial cartilages, and posterior meniscal tears was observed in 78.8% of cases. ACL degeneration was present in 54.1% of cases, while osteoarthritis was present in 78.8%. The study also introduced a novel scoring system to evaluate the severity and association of insufficiency fractures with meniscal pathology and other related factors. Conclusion: A significant association between SIFK and underlying biomechanical and degenerative factors was well appreciated. A higher incidence of SIFK was observed among females, particularly after sixth decade of life. Meniscal extrusion and cartilage loss were the common associated factors in SIFK, emphasizing the importance of early detection and appropriate management of associated degenerative changes of the knee joint so as to prevent the progression into insufficiency fractures.