Estimating a team’s win probability at any given point of a game is a common task for any sport, including esports, and is important for valuing player actions, assessing profitable bets, and engaging fans with interesting metrics. Past studies of win probability in esports have relied on data extracted from matches held in well-structured and organized professional tournaments. In these tournaments, players play on set teams, oftentimes where players are well acquainted with all participants. However, there has been little study of win probability modeling in casual gaming environments – those where players are randomly matched – even though these environments form the bulk of gaming hours played. Using interpretable win probability models trained on large CSGO data sets, we improve upon the current state of the art in Counter-Strike: Global Offensive (CSGO) win probability prediction. We identify important features, such as team HP and equipment value, across different skill levels. We also find a small benefit to using Elo-based player skill estimates in predicting win probability. Furthermore, we discuss how our win probability models can be used to investigate the problem of player-leaving in competitive matchmaking.