Vaginal pessaries have long been used in the management of pelvic organ prolapse as an alternative option for surgery. Vaginal cancer is a very rare form of gynaecological malignancy, and its association with vaginal ring pessaries has yet to be clearly established. We examined the cases of vaginal cancers in a tertiary state hospital for the last three years and found four cases of vaginal cancers, in which three of these cases were associated with a long history of using vaginal ring pessary for pelvic organ prolapse. Two of them had defaulted follow- up and presented with a vaginal mass and vaginal bleeding. These two cases did not have evidence of distant metastases, one of them underwent surgical removal of the tumour and radiotherapy, whilst the other case was initially given neoadjuvant chemotherapy, but the patient died prior to her planned surgery. The third patient declined further investigation and treatment after she was diagnosed with vaginal cancer. In conclusion, such potential serious long term complication from vaginal pessary should be informed prior to its insertion, it is also imperative to ensure compliance to regular follow- up for patients on vaginal pessaries, and to biopsy any suspicious chronic vaginal ulcers.