Ice hockey is a collective competitive sport played on ice, in which ice skates, puck, and hockey sticks are used as the tools to play against another team. Two teams per game and has six players on each team. The six players on the ice are divided into three forwards, two defensemen, and one goaltender. National Hockey League (NHL) is the professional sports league composed of North American ice hockey teams. It is the highest level professional hockey game in the world and one of the four major professional sports in North America. NHL is divided into the regular season and the playoffs. The regular season plays 82 games (41 home games and41 away games). Each NHL regulation game is 60 minutes long, and it consists of three 20 minutes periods with an intermission in between. For each game, NHL only allows a maximum of 20 players on each team, with 18 skaters and two goaltenders. And the players must be on the list of a 23-player active roster. This thesis is aiming to predict and simulate the upcoming NHL seasons. The result of the prediction is based on the in-season and pre-season game features and will be predicting not only the probability of winning the championship, but also the possibility of each team get up to different stages. The prediction will be done by using machine learning algorithms and the ELO rating system will analyze and compare the results of the algorithms.