On-field, the season saw Riewoldt continue his transition to the centre half forward position. He improved his endurance, agility and leaping ability by shedding weight and focusing on the game further from the goal-line. He suffered a minor ankle injury in round 5 and required an intense program of icing and rehabilitation to be ready for his club's round 6 match with . He played in his 200th career game in round 21's loss to Geelong at the MCG. Riewoldt ultimately played in each of Richmond's 22 games in 2016, kicking a team leading 48 goals. It was the first time he went without kicking a bag of five goals in a match since his eight-game debut season. He did however set a new personal best in total and average disposals, playing his new role closer to the midfield. Riewoldt placed fourth at the club's best and fairest count, securing the Fred Swift medal as a result.