Background and Objectives: Intramedullary nailing of trochanteric fractures can be challenging and sometimes the clinical situation does not allow perfect implant positioning. The aim of this study was (1) to compare in human cadaveric femoral heads the biomechanical competence of two recently launched cephalic implants inserted in either an ideal (centre–centre) or less-ideal anterior off-centre position, and (2) to investigate the effect of bone cement augmentation on their fixation strength in the less-ideal position. Materials and Methods: Fourty-two paired human cadaveric femoral heads were assigned for pairwise implantation using either a TFNA helical blade or a TFNA screw as head element, implanted in either centre–centre or 7 mm anterior off-centre position. Next, seven paired specimens implanted in the off-centre position were augmented with bone cement. As a result, six study groups were created as follows: group 1 with a centre–centre positioned helical blade, paired with group 2 featuring a centre–centre screw, group 3 with an off-centre positioned helical blade, paired with group 4 featuring an off-centre screw, and group 5 with an off-centre positioned augmented helical blade, paired with group 6 featuring an off-centre augmented screw. All specimens were tested until failure under progressively increasing cyclic loading. Results: Stiffness was not significantly different among the study groups (p = 0.388). Varus deformation was significantly higher in group 4 versus group 6 (p = 0.026). Femoral head rotation was significantly higher in group 4 versus group 3 (p = 0.034), significantly lower in group 2 versus group 4 (p = 0.005), and significantly higher in group 4 versus group 6 (p = 0.007). Cycles to clinically relevant failure were 14,919 ± 4763 in group 1, 10,824 ± 5396 in group 2, 10,900 ± 3285 in group 3, 1382 ± 2701 in group 4, 25,811 ± 19,107 in group 5 and 17,817 ± 11,924 in group 6. Significantly higher number of cycles to failure were indicated for group 1 versus group 2 (p = 0.021), group 3 versus group 4 (p = 0.007), and in group 6 versus group 4 (p = 0.010). Conclusions: From a biomechanical perspective, proper centre–centre implant positioning in the femoral head is of utmost importance. In cases when this is not achievable in a clinical setting, a helical blade is more forgiving in the less ideal (anterior) malposition when compared to a screw, the latter revealing unacceptable low resistance to femoral head rotation and early failure. Cement augmentation of both off-centre implanted helical blade and screw head elements increases their resistance against failure; however, this effect might be redundant for helical blades and is highly unpredictable for screws.