The aim of the study was to evaluate microleakage and the penetration-depths of different fissure-sealant materials applied with/ without enameloplasty after cyclic aging. One-hundred-sixty mandibular molars were divided into non-invasive and enameloplasty preparation groups and eight material subgroups, including: flowable composites (microhyrid, nanohybrid, and nanofilled), three resin-based (unfilled, filled, and highly-filled), a giomer-based, and a glass-ionomer-based fissure sealant. Specimens were subjected to two-year cyclic chewing and brushing simulation. After 5% basic-fuchsin dye penetration, specimens were sectioned and scored under stereomicroscope. Kruskal-Wallis statistical data showed that preparation type significantly affected the penetration of all tested materials (p<0.05), but not significantly affected microleakage (p>0.05). Flowable composites showed the best and the glass-ionomer-based sealant showed the worst penetration and microleakage. Slight preparation of fissures is not important in microleakage. However, enameloplasty significantly enhanced the depth of penetration of the sealants. Flowable composites offer promising results at the fissure sealing.