In the 2019/20 off-season, Pickett was awarded Richmond life membership for playing in the club's 2019 premiership-winning team. He completed a full load of pre-season training and maintained a place in the club's best 22 through each of its two pre-season series matches, before earning selection in the season-opening match against Carlton. Pickett recorded 14 disposals and an equal match-high five tackles in the win, played under extraordinary conditions imposed on the league as a result of the rapid progression of the coronavirus pandemic into Australia. In what the league planned would be the first of a reduced 17-round season, the match was played without crowds in attendance due to public health prohibitions on large gatherings and with quarter lengths reduced by one fifth in order to reduce the physical load on players who would be expected to play multiple matches with short breaks in the second half of the year. Just three days later, the AFL Commission suspended the season for an indefinite period after multiple states enforced quarantine conditions on their borders that effectively ruled out the possibility of continuing the season as planned. Pickett contributed just seven disposals in a round 2 draw with when the season resumed in early-June following an 11-week hiatus. He was again subdued with 10 disposals in round 3, before being omitted from the club's round 4 side. Instead, he took part in an unofficial scratch match against 's reserves players due to the cancellation of the VFL season. He played one further reserves match the following week before the main playing group was relocated to the Gold Coast in response to a virus outbreak in Melbourne. Pickett earned an AFL recall in place of injured midfielder Dion Prestia in round 6, before an injury to Josh Caddy the following week allowed Pickett to cement a place of the wing in late July and early August, including with back-to-back 14 disposal and one goal games against the and in rounds 9 and 10 respectively. Pickett posted then career-bests in marks (six), inside-50s (nine), metres gained (602) and uncontested possessions (15) in round's Dreamtime in Darwin win over , before earning one Coaches Association Award vote in round 15 for a performance that included 19 disposals and four score involvements. Pickett turned in modest performances when the finals series began, adding 12 disposals in a first-up qualifying final loss to the . He was praised by coach Damien Hardwick for his defensive efforts in a semi-final win over a week later, before improving his offensive game with 13 deposals in a preliminary final against in the third week of the finals. One week later, Pickett became a two-time AFL premiership player in just his 20th appearance, as Richmond defeated at the Gabba to claim a second successive premiership. He contributed 14 disposals in the win and was praised by AFL Media for his dedication to push back from the wing into defensive 50 to assist his teammates' defensive efforts. He finished the season having played 19 of a possible 21 games, placing 18th in the club's best and fairest count.
