Fluoroquinolone use is associated with the development of tendinopathy, most commonly affecting the Achilles tendon. Here we present the first reported case of bilateral iliopsoas tendon rupture associated with prolonged ciprofloxacin use. This older woman presented with non-traumatic, sudden onset hip pain which was diagnosed as a right iliopsoas rupture on MRI. Despite stopping ciprofloxacin, she went on to develop rupture of the contralateral iliopsoas tendon. This case highlights the time lag between fluoroquinolone use and susceptibility to this rare but important complication.