Objectives The aim of the study was to evaluate the 5-year clinical performance of occlusal carious restorations using nanofill and microhybrid composites, in combination with 3-step etch-and-rinse adhesives, in patients who were going to commence orthodontic treatment. Materials and Methods A total of 118 restorations for occlusal caries were conducted prior to orthodontic treatment. Occlusal restorations were performed both with Filtek Supreme XT (3M ESPE) and Filtek Z250 (3M ESPE) before beginning orthodontic treatment with fixed orthodontic bands. Restorations were clinically evaluated at baseline and at 1, 2, 3, 4, and 5-year recalls. Results None of the microhybrid (Filtek Z250) and nanofill (Filtek Supreme XT) composite restorations was clinically unacceptable with respect to color match, marginal discoloration, wear or loss of anatomical form, recurrent caries, marginal adaptation, or surface texture. A 100% success rate was recorded for both composite materials. There were no statistically significant differences in any of the clinical evaluation criteria between Filtek Z250 and Filtek Supreme XT restorations for each evaluation period. Conclusions The composite restorations showed promising clinical results relating to color matching, marginal discoloration, wear or loss of anatomical form, recurrent caries, marginal adaptation, and surface texture at the end of the 5-year evaluation period.