Objective: The purpose of this study was to evaluate microleakage of Single-bond and Prompt L- pop in different periods of time. Methods: Non-retentive cavities were prepared on buccal surfaces of 60 human bicuspids with no defect. They were candidates for extraction because of orthodontic reasons. The cervical margin of the cavities was in dentin and the occlusal margins were in enamel. Two bonding systems: Single-bond (3M)(Total etch system) and Prompt L-pop (3M-ESPE) (Self etch system) were used and then cavities were restored with filtek Z250 composite resin (3M). The samples were extracted after three periods of time: immediately, one week and six months. Apical foramina and surfaces around the restoration were coated with nail varnish, then immersed in 50% silver nitrate solution, mounted and sectioned longitudinally and microleakage scores were determined under stereomicroscope observation. The data were analyzed by Mann Whitney and Wilcoxon tests. Results: Although single-bond results were better than Prompt L-pop in enamel margins, only after one week the difference was significant (P-value=0.019). Results of both systems in dentin margins were similar but the difference in immediately group was significant (P-value=0.029). Enamel microleakage of all Single-bond groups was less than dentin microleakage (P-value<0.05), time had no effect on enamel microleakage but there was a significant difference of dentin microleakage between immediately group and one week group (P-value=0.01). Time had no effect on enamel and dentin microleakage of all Prompt L-pop groups, but after six month, the difference between enamel micro-leakage and dentin microleakage was significant (P-value=0.035). Conclusions: Almost all the groups had different scores of microleakage. The results of this in-vivo study showed that with these systems, bonding to enamel was more durable than dentin. Prompt L-pop less affected dentinal seal during time.

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