I'd make it a simple board game like shoots and ladders. The numbered spaces basically correspond to how many points your team has, and the players would effectively be the teams. The team that finishes first gets the max amount of points, and at that point the season would end and everyone else would have their point totals. You could presumably do a playoff afterwards with the top teams, and whichever one wins that wins the Challenge Cup. The ladders would correspond to things that usually mean a team is streaking positively, like a hot goalie, a long stint of playing on home ice, playing against struggling teams, team psychologists sessions, etc. The shoots would correspond to negative things, like star players being injured, running into hot teams, a bad trade needed for cap space, a long away stint, a coach needed to be fired, etc. The board itself would get a thematic overhaul to include all sorts of SHL and hockey references to make it feel like it's embodying a journey through a season.