Roller skiing is one primary form of training method as it is an off-snow equivalent to cross-country (XC) skiing during the dry land preseason training, but the results could only be applied to on-snow skiing with appropriate caution. The aim of this present study was to investigate the similarities and differences in roller skiing and on-snow skiing with the diagonal stride (DS) technique. Six youth (age: 14.3 ± 2.9 years) skiers participated in this study. Two high-definition video camcorders and FastMove 3D Motion 2.23.3.3101 were used to obtain the three-dimensional kinematic data. The cycle characteristics and joint angle ROM of the DS technique while skiing on different surfaces were similar. Almost all joint angle–time curves that were obtained from roller skiing showed a moderate-to-high degree of similarity to the angle–time curves obtained from on-snow skiing, except the hip adduction–abduction angle. The differences between roller skiing and on-snow skiing were mainly found in the body and calf anteversion angles, and the joint angles at critical instants. DS roller skiing can simulate DS on-snow skiing to a large extent in youth athletes. The hip movement, knee flexion, and calf anteversion at ski/roller ski touchdown and take-off, pole inclination at pole touchdown, body anteversion angle, and trunk anteversion angle at pole touchdown were the points that required caution when transferring preseason practice roller skiing to on-snow skiing.