Fluoroquinolone-induced tendinopathy (FIT) is a recognized adverse drug reaction characterized by tendon pain, inflammation, and, in more severe cases, spontaneous tendon rupture. Although the Achilles tendon is affected in up to 90% of reported cases, injuries to other tendons remain underreported. We present an unprecedented case of a 41-year-old female patient, eutrophic and previously musculoskeletal healthy, who developed sudden, severe left hip pain radiating to the gluteal region and posterior thigh, associated with limping and functional impairment, 14 days after completing a five-day course of ciprofloxacin (500 mg) for urinary tract infection. Physical examination revealed localized tenderness over the left gluteal region without radicular neurological signs. MRI demonstrated partial rupture of the gluteus medius tendon at its insertion on the greater trochanter, accompanied by trochanteric bursitis. Application of the Naranjo algorithm yielded a score of 6, indicating a probable causal relationship between drug exposure and injury. The patient had a remote history of corticosteroid use and cervical discectomy, but no concurrent medications increasing risk. Treatment consisted of analgesia, NSAIDs, orthosis, and physiotherapy, with complete symptom resolution after approximately six weeks. The incidence of FIT ranges from 0.14% to 2.0%, being more common in elderly patients, those on corticosteroids, or with predisposing comorbidities. The risk of tendon rupture is up to 4.1 times higher among fluoroquinolone users, with peak occurrence 6–14 days after exposure. Pathophysiologically, FIT involves inhibition of tenocyte proliferation, increased metalloproteinase activity, and oxidative stress on the tendon’s extracellular matrix. The present case expands the clinical spectrum of FIT by documenting, for the first time in the literature, gluteus medius tendon rupture associated with ciprofloxacin, highlighting the need for clinical vigilance in patients presenting new musculoskeletal symptoms after fluoroquinolone use, even in the absence of classical risk factors, and the importance of early diagnosis to prevent disabling outcomes.