Following his rookie season, Landry became a restricted free agent. However, his contract negotiations with Houston Rockets showed little progress. On September 24, 2008, he received a three-year, $9 million offer sheet from the Charlotte Bobcats. One day later, the Rockets matched the offer. On November 26, 2008, teammate Tracy McGrady sat out of a game against the Indiana Pacers. Landry came off the bench and put up 15 points and grabbed 10 rebounds for a double-double. Another career game for Landry during the 2008–09 season came on January 3, 2009 against the New Jersey Nets, where he led the team in scoring with 18 points by making 5-of-5 shots from the floor and going 8-of-8 from the free throw line. Being the team's sixth man and averaging over 21 minutes per game, he averaged over nine points and five rebounds during the regular season, while leading the Rockets with a .574 field goal percentage.