Winter Challenge features two modes. In Tournament mode, the player can create a competitor and participate with up to ten players, with selectable names, countries and user pictures. Once the players are selected, the game shows an opening ceremony for the tournament and then takes the player to a tournament screen where they can see their icons for the events, as well as four buttons that shows their current standings, starts a new tournament, allows the entering of a password to return to an existing tournament, or return to the main menu. In this mode, computer-generated opponents have a skill level, from 'Amateur' to 'Professional' and 'World Class', affecting their speed and stamina in events. In Training mode, the player can participate in a single event as one player. Several events are simplified for the training mode to allow error, such as being able to miss flags in the giant slalom. Once completed, the player can play again, return to the main menu, or watch an instant replay of their performance.
