Sessions scored in double figures five times to finish the 2007–08 season, including two games of 20 points or more, and handed out double-figure assists six times, tallying three double-doubles. He scored 20 points and handed out a career-high and Bucks franchise record 24 assists on April 14 against the Chicago Bulls, becoming the first player in team history to record 20 points and 20 assists in the same game. His 24 assists was the third-highest single-game total by a rookie in NBA history. He went on to score a season-high 25 points with 14 assists on April 16 against the Minnesota Timberwolves. He handed out double-figure assists in five straight games to end the season and was subsequently named Eastern Conference Rookie of the Month for April.