Jackson followed his strongest season as a pro with an even stronger one during the 2009 season, when he finished with 68 receptions, and led the team in receiving with 9 touchdowns and 1,167 yards. During a January 17, 2010 divisional playoff game against the New York Jets, Jackson made a 37-yard catch that was challenged by Jets head coach Rex Ryan. Jackson received an unsportsmanlike conduct penalty for kicking the challenge flag, which cost the Chargers 15 yards (the play was upheld). Jackson would finish the game with 7 receptions for 111 yards, becoming the first receiver of the 2009 NFL season to record a 100-yard game on the Jets All-Pro cornerback and future Buccaneer teammate Darrelle Revis.