Australia in the 2017 International Rules Series and was awarded the Jim Stynes Medal. (best player in the series). Fyfe missed out on the All-Australian Team, not even being named in the initial 40-man squad. He polled 15 votes at 2017 Brownlow Medal, finishing 11th. In July 2017, Fyfe signed a six-year contract extension with Fremantle – the longest contract extension in the club's history – tying him to the Dockers until 2023. Fyfe was in career-best form at the start of the 2018 AFL season, playing a match-winning hand in a number of the club's early wins. This included a career-best 43 disposals against the Western Bulldogs and 14 clearances against Gold Coast. In his 150th senior appearance for Fremantle, Fyfe recorded 30 disposals, 2 goals, and 7 inside-fifties, along with earning a goal of the year nomination for his crafty snap against Carlton in the 57-point win. Fyfe suffered a hamstring injury in Fremantle's Round 15 clash against the Brisbane Lions, hobbling off in the first quarter, and resulting in him spending six weeks on the sidelines. Fyfe returned in Fremantle's Round 22 clash against Geelong, recording 37 disposals and 7 clearances, despite the best on ground performance, Geelong demolished Fremantle by 133 points. Fyfe once again missed the All-Australian Team, not making the 40-man squad. 2019–present: Career-best form and second Brownlow Medal Fyfe started the 2019 AFL season strongly, recording 32 disposals, 8 inside-fifties, and 10 clearances in Fremantle's Round 1 clash against North Melbourne, Fyfe followed up that performance with a similar one the next week, recording 31 disposals and 9 clearances. Fyfe continued this form throughout the season and was considered as being one of the favourites to win the Brownlow Medal. Fyfe finished the season with a career-high disposals (583) and a career-high average, increasing his disposal average to 29.2. Fyfe made the 2019 All-Australian Team, his first time making it since 2015, and was named Captain of the team for the first time in his career. Fyfe won his second Brownlow Medal, becoming a dual Brownlow Medallist, and becoming the 15th player in VFL/AFL history to win it twice, Fyfe polled a career-high votes (33), beating out the runner-up Patrick Dangerfield by 6 votes (27 votes). After a good start to the 2020 season, which was impacted by the COVID-19 pandemic, Fyfe suffered a minor hamstring injury in Round 4 against Gold Coast.