Reversible and switchable adhesion of elastomeric microstructures has attracted significant interest in the development of grippers for object manipulation. Their applications, however, have often been limited to dry conditions and adhesion of such deformable microfibrils in the fluid environment is less understood. In the present study, we performed adhesion tests in silicone oil using single cylindrical microfibrils of a flat-punch shape with a radius of 80 µm. Stiff fibrils were created using three-dimensional printing of an elastomeric resin with an elastic modulus of 500 MPa, and soft fibrils, with a modulus of 3.3 MPa, were moulded in polyurethane. Our results suggest that adhesion is dominated by hydrodynamic forces, which can be maximized by stiff materials and high retraction velocities, in line with theoretical predictions. The maximum pull-off stress of stiff cylindrical fibrils is 0.6 MPa, limited by cavitation and viscous fingering, occurring at retraction velocities greater than 2 µm s−1. Next, we add a mushroom cap to the microfibrils, which, in the case of the softer material, deforms upon retraction and leads to a transition to a hydrostatic suction regime with higher pull-off stresses ranging from 0.7 to 0.9 MPa. The effects of elastic modulus, fibril size and viscosity for underwater applications are illustrated in a mechanism map to provide guidance for design optimization.