Riewoldt played his junior and early senior football for the Broadbeach Cats before moving to the Southport Sharks where he was identified as an outstanding junior talent. He played a big part in Southport’s historic fourth consecutive QAFL premiership in 2000. After being kept virtually touchless for the first half, he was moved into the ruck and kicked two important goals in the 11-point grand final victory.

Riewoldt was the No. 1 Draft Pick in the 2000 AFL Draft and made his debut in 2001.

His breakout season was 2004 when he took an AFL record 256 marks and also finished in the top ten for both the Coleman and Brownlow medals. He received the AFL Players Association Most Valuable Player Award, the Leigh Matthews Trophy and was selected in the 2004 All-Australian Team for the first time.

Early in the 2006 season, Riewoldt returned close to his best form, kicking five goals against former powerhouse Brisbane in Round 3. This match seemed to have put Riewoldt’s kicking “yips” to bed, but they returned during the Round 7 match against Geelong when he missed a simple but critical goal from 15 metres out. This miss was forgotten the next week when Riewoldt kicked 9 goals against Carlton and took many contested marks. Riewoldt also took a match saving mark for the Saints against Sydney in Round 11, a match the Saints won in wet conditions, and one that kept their finals hopes alive.

Riewoldt topped off the 2006 season by winning his third Trevor Barker Award. In achieving this feat, Riewoldt has already emulated some of the Saints greatest players such as the 1966 premiership captain Darrel Baldock, former skipper Nathan Burke and past champions Wells Eicke, Jack Davis and Jim Ross. Riewoldt was recognised for his season with selection in the 2006 All-Australian Team as a forward player, his second career All-Australian Team award.

Riewoldt played in St Kilda’s 2008 NAB Cup winning side – the club’s third pre-season cup win. Riewoldt had a consistent 2008 season, coming second in the AFL for marks (behind Matthew Richardson) and kicking 57 home and away season goals (63 all up) to finish ninth in the competition. This performance earned him his third All-Australian selection, his first at centre-half-forward. He was also selected to play in the Hall of Fame Tribute Match, but was ultimately unable to play due to a knee injury. Riewoldt was recognised for his season with selection in the 2008 All-Australian Team as a forward player. This was his third All-Australian Team award.

Riewoldt played in 21 of 22 matches in the 2009 home and away rounds in which St Kilda qualified in first position for the finals series, winning the club’s third minor premiership.

Riewoldt was recognised for his season with selection in the 2009 All-Australian Team as a forward player. He was also named captain of the 2009 All-Australian Team, his fourth All-Australian Team award.

Riewoldt won the 2009 Trevor Barker Award for St Kilda’s best and fairest player, setting a new club record of five career best and fairest awards. He was also St Kilda’s leading goal kicker in 2009.

During St Kilda’s 28-point Round 3 win over Collingwood, on 9 April 2010, Riewoldt experienced a high grade hamstring tear. He underwent surgery and made his return in Round 15, playing 15 games in the season for 39 goals.

Early in the season Riewoldt became a target for the fledgling Gold Coast Football Club, which was awarded the 17th licence to enter the AFL in 2011. However, he knocked back their offer to remain at St Kilda.

Riewoldt is married to Catherine Heard. The pair married in October 2012 at her parents’ property in Waco, Texas, United States. They have three sons, James (born in 2014), William (born in 2016), and Edward “Teddy” (born 2019). His sister Madeleine died of aplastic anaemia, a rare bone marrow condition, in February 2015 at the age of 26. Riewoldt and his family established Maddie’s Riewoldt’s Vision to raise funds for research into new treatments for blood cancers.

On 1 September 2016, at the Saints’ best-and-fairest awards night, Riewoldt announced that he would stand down as St Kilda captain.

On 31 July 2017, Riewoldt announced that he would retire at the end of the season. He played the final game of his career in round 23 when he had 15 disposals, 8 marks and 1 goal in a loss to the Richmond Tigers, his cousin’s team.