In 2008, Ray completed 422 of 608 pass attempts (69.8% completion) for a league-leading, career-best, and single-season Eskimo record 5,661 yards. Ray threw for 26 touchdowns and 17 interceptions for a 101.8 quarterback rating. Ray also scrambled for 258 yards and 5 touchdowns. One of his best games of the season came in the final week of the season vs. the Alouettes when Ray broke the record for highest completion percentage in a single game (with a minimum of 20 passing attempts) when he went 23 of 25 for 92.0% for 302 yards and 2 touchdowns in only 3 quarters of play. He led the Esks to a win in the crossover playoff game in Winnipeg, but the team lost in the East finals to Montreal. The 2008 Eskimos were the first team to ever win a crossover game.