This study evaluated the influence of fluoride-containing carbamide peroxide (CP) bleaching agents and adhesive systems on bonded enamel interfaces that are part of the dynamic pH cycling and thermal cycling models. The buccal surfaces of 60 bovine incisors were restored with a composite resin and bonded with three- and two-step, etch-and-rinse, fluoride-containing adhesives, Optibond FL (FL) and Optibond Solo Plus (SP), respectively. Restored teeth were subjected to thermal cycling to age the interface. Both SP and FL adhesive-restored teeth were bleached (n = 10) with 10% CP (CP) and 10% CP + fluoride (CPF) or were left unbleached (control). Bleaching was performed for 14 days simultaneously with pH cycling, which comprised of 14 h of remineralization, 2 h of demineralization and 8 h of bleaching. The control groups (FL and SP) were stored in remineralizing solution during their bleaching periods and were also subjected to carious lesion formation. Parallelepiped-shaped samples were obtained from the bonded interface for microtensile bond strength (∝TBS) testing. The enamel ∝TBS of the FL and SP groups (control, not bleached) were higher (p < 0.05) than those of the bleached interfaces (FL > FL + CPF = FL + CP and SP > SP + CPF = SP + CP). The groups subjected to treatment with the fluoride-containing bleaching agents exhibited similar ∝TBS compared to regular bleaching agents. Bleaching agents, regardless of whether they contained fluoride, decreased enamel bond strength.