To compare the effect of two bleaching systems (bleaching gel and whitening strips) on the color change, roughness, and microhardness of enamel and two resin composites. Two cavities were prepared on bovine enamel specimens (n = 16) and restored with two composites: a nano-hybrid [Herculite Ultra (HU)] and a micro-hybrid composite [TPH Spectra (TS)]. Baseline color (CIE L*a*b*), roughness (μm), and microhardness (kgf/mm2) were measured using a spectrophotometer, optical profilometer, and Vickers microhardness (VHN) tester, respectively. The specimens were stained with coffee for 14 days, and randomized into two bleaching groups: gel and strips (n = 8), then submitted to a 10-day bleaching/staining test. Color, roughness, and microhardness were re-measured. The outcomes were analyzed using two-way ANOVA and Fisher’s-PLSD test (α = 0.05). Gel significantly improved the color (ΔE 4.9–8.3) and increased the roughness (Ra 0.04–0.08 μm) of all substrates (p < 0.0001) compared to strips. Enamel color was significantly improved (ΔE 5.4–8.3) compared to that of HU (ΔE 2.6–4.9) and TS (ΔE 2.0–4.9) with either gels or strips. TS roughness (0.03–0.08 μm) was significantly higher than that of enamel (0.01–0.05 μm) and HU (0.02–0.04 μm). Enamel had significantly reduced microhardness compared to HU (p = 0.0144). Gels produced the greatest color improvement and roughness compared to strips. Enamel had significant color improvement but had the greatest decrease in microhardness. There was unacceptable color change between enamel and the composites after the combined cyclic effects of staining and bleaching.