Cervical cancer is a largely preventable disease, with over 90% of cases caused by persistent infection with human papillomavirus (HPV). Despite the availability of HPV vaccination and cervical screening, incidence rates in Canada have been rising since 2015, particularly among underserved populations. This study investigates contributing factors behind cervical cancer diagnoses in Eastern Ontario over a two-year period to identify gaps leading to failures in prevention and screening. A retrospective chart review was conducted for cervical cancer cases diagnosed between January 2022 and December 2023 at two regional cancer centres in Eastern Ontario. Cases were categorized as screen-detected, inadequately screened, or system failure, based on prior screening history and care processes. Data was collected on patient, screening, and cancer characteristics. Of 132 cases, 22 (16.7%) were screen-detected, 73 (55.3%) were inadequately screened, and 37 (28.0%) were attributed to healthcare system failure. Later-stage disease was significantly more common in the latter two groups. Thirty-one (23.5%) cases presented with palliative diagnoses, and 18 (13.6%) individuals died within 2.5 years. Inadequate screening was associated with rurality, deprivation, and lack of a primary care provider. System failures included false-negative Pap tests, loss to follow-up, and misapplication of screening guidelines. This study evaluated failures in cervical cancer prevention, which led to cervical cancer diagnoses in Eastern Ontario. Gaps included suboptimal screening participation, lack of access to care, health care system breakdowns, and limitations of the Pap test. Findings provide concrete suggestions for eliminating cervical cancer in Canada.