(1) Background: The aim of the present in vitro investigation was to evaluate, on polyurethane sheets, two different drilling techniques for dental implant positioning using osteocondensing burs compared to a standard type protocol. (2) Methods: Three different implant designs (Implacil De Bortoli UN III 4 × 10 mm, Restore RBM 4 (HEX) × 10 mm; Implacil De Bortoli UN II 4 × 10 mm) were evaluated (test implant (osteocondensing drills) and control implant (standard drills)). The insertion torque (IT), the removal torque (RT) and the resonance frequency analysis (RFA) values of test and control implants inserted in different size and different density polyurethane foam models were compared for 120 experimental sites. Accordingly, 120 experimental holes were produced in different PCF polyurethane foams: 60 sites were produced in 10 PCF sheets and 60 sites in 10 PCF sheets with an additional 1 mm layer of 30 PCF. (3) Results: The IT, removal torque and RFA values were significantly higher for both of the evaluated implants, in the sites prepared with the osteocondenser drills when compared to sites prepared with standard drills (p < 0.05). The UNII and UN III showed significantly higher stability compared to the HEX implant; these differences increased drastically in the 10 PCF Polyurethane Block with the additional 1 mm cortical layer (p < 0.05). (4) Conclusions: The outcome of this investigation suggested a possible clinical application of osteocondensing burs in case of reduced bone quality and quantity in the posterior maxilla.