Cervical leiomyoma is a relatively uncommon type of uterine leiomyoma. Prolapse of a cervical leiomyoma with inversion of the cervix is an extremely rare phenomenon, especially in a non-puerperal woman. Only a handful of cases are reported in the English literature. The case discussed here is of a vaginal prolapse of a submucous cervical fibroid complicated by cervical inversion in a South Asian perimenopausal woman with multiple comorbidities who had defaulted medical follow-up during the second wave of the COVID-19 pandemic. Being one of the largest reported cervical fibroids to date is another particularity of this case. Emphasis is given to the clinical diagnostic, anaesthetic, and surgical challenges encountered with a brief note on the impact of COVID-19 on outpatient clinic follow-up.