In 2008–09, Sessions scored in double figures 53 times, including 12 games with 20 points or more and one game with 40 points or more. He handed out double-figure assists 10 times, grabbed double-figure rebounds once, tallied nine double-doubles, and had one triple-double. He scored a career-high 44 points and handed out 12 assists on February 7 against the Detroit Pistons, setting career highs of 13 field goals, 18 free throws and 21 free-throw attempts. Four days later, he had 15 points and a season-high 17 assists against the Indiana Pacers. He recorded his lone career triple-double with 16 points, 16 assists and a career-high 10 rebounds on April 1 against the Los Angeles Lakers. He led the Bucks in scoring nine times, in assists 43 times and in steals 20 times.