The purpose of this study was to investigate the biomechanics of cross-country sit-skiing in simulated and natural skiing. Thirteen international level athletes participated in a ski ergometer test (simulated conditions) and a test on snow in a ski-tunnel (natural conditions) using their personal sit-ski. Tests in both conditions were performed at individual maximal speed. When comparing the two conditions the main results were: (1) maximal speed in simulated conditions was lower (p < 0.05) but correlated well with the natural condition (r = 0.79, p < 0.001); (2) no differences in pole force variables were found; peak force (r = 0.77, p < 0.01) and average force (r = 0.78, p < 0.01) correlated well; (3) recovery time and time to peak did not differ and time to impact correlated with each other (r = 0.88, p < 0.01); (4) no differences were found in peak electromyography (EMG) and average EMG for Triceps, Pectoralis, and Erector Spinae; Rectus Abdominis did not differ in peak. EMG peak and average EMG of all muscles were correlated between the two conditions (r = 0.65–0.94; p < 0.05–0.01). Although some differences were observed, this study demonstrated that technical skill proficiency in natural and simulated cross-country skiing is comparable from a force production and muscle activation perspective.