Fetal maceration and pyometra were diagnosed in a 16-year-old maiden Welsh pony mare. Due to anatomical and surgical difficulties encountered throughout treatment, previously reported techniques including both per-vaginum removal of fetal remnants and ovariohysterectomy were attempted and resulted in novel complications. Fetal bones were unable to be removed completely transcervically due to failure of cervical dilation despite repeated attempts. Subsequent surgical complications such as inadequate exposure of the uterus and incorporation of fetal bones into the uterine stump following ovariohysterectomy also occurred. This case highlights some of the difficulties in managing rare cases of mid-term fetal loss and retention that result in maceration. Ultimately, this may provide useful insights to practitioners when managing similar cases in future.