Tendinopathy is a well-defined adverse effect of fluoroquinolone (FQ) antibiotics with complete tendon rupture being the most serious consequence. The most described FQ-associated tendinopathies are of the Achilles tendon with an onset ranging between 2 h after initial FQ administration to 6 months after completing FQ treatment. We herein report the case of a 50-year-old diabetic woman who suffered from a right Achilles tendon rupture and contralateral nontraumatic tibialis anterior (TA) tendon rupture 11 and 25 months following FQ administration, respectively. Operative management of both injuries identified degenerative changes consistent with FQ treatment. This case is unusual in its involvement of an uncommon tendon in an atypical timeframe. Notably, only one other reported case of FQ-associated TA tendon rupture was identified.