[11][12] After another summer season with St Mary's, Rioli returned to Melbourne in 2019 where he joined the squad of the Oakleigh Chargers, though would not earn a top-flight NAB League match during that his 'underage' year.

[33][1] He first represented Richmond as part of the club's reserves side, featuring in VFL pre-season matches from February through April when the season officially began.

[37] Though he went unselected in the final team, he was a stand-out performer at reserves level, kicking two goals and recording 17 disposals in the opening round of the VFL season that same weekend.

[40][41] In May, Richmond senior coach Damien Hardwick labelled Rioli close to AFL selection, but said he would require a stronger endurance base before he could be named for a debut.

[43][44] Following an eight-tackle game against Frankston in early August, Rioli was elevated to senior level and named to make his AFL debut in a round 21 match against North Melbourne.

[45][46] Rioli plays primarily as a defensive small forward and is notable for his ability to apply forward-half pressure and create turnovers among opposition defenders.