(1) Background: Displaced supracondylar humeral fractures in pediatric patients can be treated by either antegrade nailing (AN) or percutaneous crossed pinning (PCP). The aim of this study was to compare the intra- and perioperative management, complications and outcome of AN and PCP. (2) Methods: This retrospective study enrolled 271 individuals (median age 5 years, IQR 4–7 years) who underwent AN (n= 173) or PCP (n= 98). Patient history was analyzed for incidence of nerve injuries, postoperative treatment, postoperative malrotation, time of hospital stay, time to implant removal and revision rate. Operative procedures were investigated for duration and radiation exposure. (3) Results: PCP was associated with a significantly lower radiation exposure (dose area product: PCP mean 20.1 cGycm2vs. AN mean 34.7 cGycm2,p< 0.001; fluoroscopy time: PCP mean 1.1 min, range 0.1–8.1 min, vs. AN mean 1.5 min, range 0.1–7.1 min,p< 0.001), duration of surgery (PCP mean 32.2 min vs. AN mean 48.3 min,p< 0.001) and time to implant removal (PCP mean 37 days vs. AN mean 113 days,p< 0.001). Cast removal was performed earlier in the AN group (PCP mean 30.2 days vs. AN mean 20.4 days,p< 0.001) and there were fewer iatrogenic nerve lesions (PCP: 24% vs. AN: 8%,p< 0.001). (4) Conclusions: In the investigated study population, the analyzed parameters seem to favor the use of PCP. The advantages of AN should be weighed against its drawbacks. For special indications, AN remains a relevant technique in supracondylar fracture treatment, and surgeons should be familiar with this procedure.