Various forms of degenerations may occur in fibroids but cystic and myxoid degenerations are not common. We reported two case series of cystic degenerations in pregnant and nonpregnant conditions. A myomectomy on pregnant uterus and total abdominal hysterectomy and bilateral salpingoophorectomy was respectively performed successfully. There was diagnostic dilemma in both cases prior to surgical intervention as available imaging investigations made diagnosis of ovarian cystic mass. Magnetic resonant imaging was not available but evidence suggests preoperative use may resolve the diagnostic dilemma.