Introduction: Pit and fissure caries account for about 90% of caries in children and adolescents. Sealant application may be a preventive conservative approach. But it's still challenging to bolster the retention of the filled sealant and to chop back the microleakage. Aim: Aim is to evaluate and compare the microleakage and shear bond strength (SBS) of three filled pit and fissure sealants (PFS) using a subpressure and adhesive system: an experimental analysis. Materials and methods: A total of 90 orthodontically extracted premolars were prepared for microleakage and SBS and divided according to materials and subgroups. Group I: resin-based filled PFS, group II: resin-modified glass ionomer-based filled PFS, and group III: giomer-based filled PFS. Subgroup 1: only sealant application, subgroup 2: subpressure application, and subgroup 3: adhesive system + subpressure application. Samples were subjected to thermocycling. Microleakage was assessed with a dye penetration method under a stereomicroscope, and SBS was assessed with a universal testing machine. Statistical analysis and results: Unpaired t-test and one-way analysis of variance (ANOVA) test were used for analysis. Significant when p < 0.05. The SBS showed significant results for subpressure application and giomer-based filled PFS with p < 0.05. The microleakages score differed significantly for the subpressure application group with p < 0.05. Giomer-based filled PFS showed the least microleakage score. Conclusion: This study concluded that giomer-based filled PFS showed statistically significant results. The subpressure technique significantly reduces microleakage and increases SBS.