Riewoldt was selected by the Richmond Football Club at 13th pick in the 2006 AFL Draft, highly rated by the Tigers as a key forward prospect.
In 2010, Riewoldt kicked a career best 10 goals in Round 12, 13 June 2010 against the West Coast Eagles. The haul included 5 first-quarter goals, with 4 of them in just 10 minutes, making it one of the best Richmond returns in a single quarter. He became the first player to kick 10 goals since 2007, and the first Richmond player since Matthew Richardson in 2004.
To cap a very successful breakout season, Riewoldt won the 2010 Coleman medal for the AFL leading goalkicker (78 goals). Four days after winning the Coleman Medal, Riewoldt secured the Jack Dyer Medal as Richmond's best and fairest with 210 votes ahead of captain Chris Newman on 204 votes and Brett Deledio on 193 votes. He was also named the All Australian full forward.
In Round 21 2010, Jack won the Ian Stewart Medal against St Kilda for his performance, kicking 7 goals.
Riewoldt continued his good form on the back of his Coleman Medal. Riewoldt placed second in the race for the Coleman behind Lance Franklin. Kicking 62 goals, Riewoldt remained one of the power forwards of the AFL at only 22 years of age.
Riewoldt once again finished at the top of his game, securing the Coleman Medal for the 2012 season in the last fixture (Round 23) against Port Adelaide. He broke a two-way tie between Matthew Pavlich of Fremantle and Tom Hawkins from Geelong, after they had played their Round 23 games first, to claim the Medal (65 goals).
On 26 July 2013, Riewoldt signed a three-year contract extension which will keep him at the club until at least the end of the 2016 season. At the time he was quoted as saying, "I genuinely love this football club and all it stands for, and I’m pleased to be part of the journey we’re on, I hope to repay the faith shown in me by the Club, and I’ll continue to give everything I have for the cause."