Cut-out is one of the most common mechanical failures in the internal fixation of trochanteric hip fractures. The tip-apex distance (TAD), and the calcar-referenced tip apex distance (CalTAD) are the radiographic parameters that most predict the risk of cut-out. The optimal CalTAD value has not yet been defined, but the optimal TAD value is reported as 25 mm or less. However, this cut-off is highly specific but poorly sensitive. The aim of this study was to determine highly specific and sensitive TAD and CalTAD values and shed light on the role of other clinical variables. A total of 604 patients were included in this retrospective cross-sectional study. For each patient the following data were recorded: number of cut-out, AO/OTA classification, quality of the reduction, type of nail, cervicodiaphyseal angle, type of distal locking, post-operative weight-bearing, TAD and CalTAD values, and the position of the screw head in the femoral head according to the Cleveland system. The incidence of cut-out across the sample was 3.1%. The median TAD in the cut-out group was 38.72, while in the no cut-out group it was 22.16. The median CalTAD in the cut-out group was 39.34, while in the no cut-out group it was 22.19. The cut-off values for TAD and CalTAD with highest value of sensitivity and specificity for the risk of cut-out were 34.8 and 35.2, respectively. The incidence of cut-out can be reduced by performing careful minimal reduction and ensuring stable fixation by avoiding TAD > 34.8 mm and CalTAD > 35.2 mm.