Purpose: The purpose of this study was to define the incidence, risk factors, and impact on survival of venous thromboembolism (VTE) recurrence in patients with genital tract malignancy. Materials and Methods: This was a retrospective cohort study of patients with gynaecological malignancies treated in the Tertiary Gynaecological Cancer Centre Hospital between 2006 and 2017. Patients with cancer-related VTE were identified. Demographic data, histology, stage, surgery, chemotherapy, co-morbidities, and timing of primary and recurrent VTE episodes were recorded. Results: One hundred and twenty-four gynaecological malignancies were diagnosed with cancer associated VTE. The incidence of recurrent VTE was 22% (n = 27). Patients were at highest risk of recurrent VTE if their first VTE had occurred before commencement of primary cancer treatment (OR 2.2, 95% CI 1.1-4.2 p = 0.018). Seventeen (63%) patients were on a therapeutic dose of low molecular weight heparin at the time of recurrent VTE. Patients with recurrent VTE had significantly higher monocyte (p = 0.03) and eosinophil count (p ≤ 0.01) compared to the non-recurrent VTE group. There was no difference in progression-free and overall survival between patients who suffered a single VTE and those who had recurrent VTE. Conclusions: Patients with gynaecological malignancies treated for VTE remain at high risk of recurrent VTE despite standard anticoagulant treatment.