[8][9] He suffered a navicular bone injury early in the year, and was held back from football duties until late into the club's inaugural season.

[12] At the conclusion of the season, it was reported that Caddy was seeking a trade to a Victorian-based club in order to be closer to his father, who was suffering a heart condition.

He was linked to Essendon in October, after reports emerged that the club had offered Gold Coast a first-round draft selection and two contracted players (Josh Jenkins and one of Scott Gumbleton or Cale Hooker) in exchange for Caddy.

[13][10] Despite AFL-led mediation conducted to help the clubs negotiate, no deal was ultimately struck, and Caddy remained at the Gold Coast after the annual trade period concluded.

[14] Despite his personal success, the poor form of the Suns meant Caddy did not play in his first AFL victory until his 17th career match, in Round 16 of the 2012 season.

[22] Despite receiving an accidental kick to the face by teammate and captain Joel Selwood (and seven stitches as a result), Caddy recorded an impressive 20 disposals and a goal in the match.

[31] The Australian Associated Press labelled Caddy's 20 disposal, two goal, round 10 performance as a continuation of "his emergence as a goal-kicking midfielder of real class.

[35][36] In the latter part of the season Caddy endured symptoms of knee tendinitis and was subbed out early in the club's round 21 match against St Kilda as a result.

[44] When Richmond's Brett Deledio began seeking a trade to Geelong in October 2016, Caddy's name was circulated in media reports concerning the potential deal.

[49] On 19 October, the day he himself had been traded to Richmond, former teammate Dion Prestia told journalists he had been in contact with Caddy in an attempt to lure him to the club.

[54] Prior to round 7 coach Damien Hardwick admitted to having played Caddy away from the ball too regularly, committing him to more midfield time in coming weeks.

[57] When full-forward teammate Jack Riewoldt sustained an eye injury, Caddy was called on to play as the team's focal point up forward.

[64][65] After featuring in each of Richmond's two pre-season matches as a forward with limited minutes in the midfield, Caddy began the 2018 season with three goals in round 1's season-opening win over Carlton.

[66][67][12] He repeated the total the following week, but was also issued a one-match suspension for striking Adelaide's David Mackay in the face with a stray fist in a marking contest during the fourth quarter of that round 2 loss.

[69][70] Upon his return in round 6, Caddy kicked a then-equal career best four goals in a win over Collingwood and was named in AFL Media's team of the week.

[73] Along with his goal tally, Caddy added 24 disposals and a game high seven tackles to earn the Ian Stewart Medal as best on ground in that win over St Kilda.

[80][81] Caddy finished the home and away season having kicked a career-best 44 goals, earning him 10th place in the Coleman Medal race for the league's leading goalkicker.

[86][87] In the ensuing preliminary final, Caddy was held goalless and with an equal season-low 11 disposals when Richmond was eliminated with a shock loss to rivals Collingwood.

[98][99] He was recalled to senior level the next week, where he contributed three goals in a win over Port Adelaide while playing as an inside midfielder and a forward in the absence of Dustin Martin.

[109][110] Though Caddy impressed as an inside midfielder with two goals and 26 disposals in that match, he remained at the lower level for a further week in or order to trial a new role as a defensive wing.

[117][118] A fortnight later Caddy's output was quieter, producing an important five intercept possessions but also recording four turnovers from just 13 disposals in his side's preliminary final victory over Geelong.

[122] After a full and uninterrupted training program in the 2019/20 off-season, Caddy resumed his role on the wing with fine performances in the pre-season series including being named by AFL Media as among the club's best players in the first of those two matches.

[127][128] Caddy contributed 15 disposals to a round 1 win over Carlton when the season began, but under extraordinary conditions imposed on the league as a result of the rapid progression of the coronavirus pandemic into Australia.

[135][136] After an 11-week hiatus, the season resumed without Caddy able to play, owing to a calf strain sustained while training in the days prior to Richmond's round 2 match.

[139][140] Caddy struggled for form early in the season restart, attracting criticisms about his suitability to a wing role from media personalities Terry Wallace and Matthew Lloyd.

[144][145][146] He could not hold his spot however, dropped back to reserves level following a poor performance that included giving up a 50-metre penalty that resulted in an opposition goal.

[149][150][151] He made a return to reserves grade football in mid-September, before being recalled for a forward line role in place of the injured Tom Lynch in the final round of the AFL regular season.

[152][153] Caddy kicked two goals in the win over Adelaide, but suffered a patella tendon injury midway through the match that left him in some doubt for the club's first round finals match-up with the Brisbane Lions.

[154][155][156] Though he was ruled fit enough to be named as an emergency in all four matches, Caddy could not break into the senior side over the course of the finals series, sidelined while his teammates earned the club a third AFL premiership in four seasons.

[161][162] He, along with teammates Dustin Martin, Reece Conca, Dion Prestia, Toby Nankervis and Anthony Miles, owns a small stake in racehorse Main Stage which ran in the 2017 spring racing carnival.