Objectives: The purpose of this in vitro study was to evaluate the microleakage in "deep" Class II composite restorations with gingival cavosurface margin below the CEJ (cemento-enamel junction) and restored with different techniques. Study Design: Fifty human teeth were used. In each tooth two standardized Class II slot cavities (on mesial and on distal surfaces) were prepared: the buccolingual extension of the cavities was 4 mm; the gingival wall was located in dentin/cementum (2 mm beyond the CEJ). The prepared teeth were randomly assigned to 5 experimental groups (of 10 specimens and 20 cavities each) and restored. Group 1: Filtek TM Supreme XTE Flowable (3MESPE) + Universal Filtek Supreme XTE (3MESPE), Group 2: GrandioSO Heavy Flow (Voco) + GrandioSo (Voco), Group 3: SDRTm (Dentsply Caulk) + Esthet-X® HD (Dentsply Caulk), Group 4: SonicFill (Kerr), Group 5: Grandio (Voco). After thermocycling, the specimens were immersed in a 0.5% basic fuchsine dye solution and incubated at 37°C for 24 hours. The teeth were subsequently sectioned mesiodistally. All specimens were examined at 25× in a stereomicroscope and standardized digital images were obtained. Dye penetration was measured from gingival margins. Results: The results demonstrated no significant leakage differences between Group 4 and Group 5, that both showed significantly higher frequency distribution of Score 0. Group 2 and Group 3 showed a significant prevalence of Score 1, whereas Group 1 showed significantly higher frequency of Score 2. Conclusions: None of the restorative techniques tested completely eliminated microleakage dye penetration in dentin margins; marginal adaptation in Class II composite restorations with gingival wall below the CEJ varied in both substrates and from different restorative techniques used.