Sicily's junior career was spent playing for the Keilor Football Club.[1] In 2013, Sicily kicked 26 goals from 16 games for the Western Jets and represented Vic Metro at the National Championships.[2]
Sicily also played for Melton bloods football club
AFL career
Sicily was drafted by the Hawthorn Football Club with the fifty-sixth pick in the 2013 AFL draft.[1] In 2014, he was widely considered Box Hill’s best player in the losing grand final, kicking a team-high three goals, and finishing with 15 disposals and five marks.[3]
He made his AFL debut against Essendon in round 2, 2015 starting as the sub. He came on replacing the injured James Frawley in the first quarter and later kicked a goal. He went on to play three games for the year.[4]
In the absence of the injured Jarryd Roughead, Sicily was named in Hawthorn's team for the opening round of the 2016 AFL season, kicking 4 goals against West Coast in round 2 and kicking the match winning goal in round 3 against the Western Bulldogs.[5][6] He was named as the round 13 nominee for the Rising Star after kicking a career high five goals and recording 13 disposals and 5 marks.[7] 2016 was regarded as Sicily's breakout season.[5]
During the 2017 season, Sicily, who had previously been a forward, was shifted to the backline, after being dropped from the team while playing as a forward.[8] He impressed in that position, but nonetheless at the end of the season was still the subject of some uncertainty around his position in the team.[9] On August 22, 2017, Sicily signed a three-year contract extension keeping him at the club until 2020.[10]
Sicily was suspended for one match in the early stages of the 2018 season for kneeing Geelong captain Joel Selwood.[11] Notwithstanding this, Sicily was widely tipped to be on track for a nomination to the All-Australian team of that year before breaking bones in his wrist in Round 17, only returning during the finals series.[12] Despite this injury, Sicily had a season widely perceived as excellent,[12] and was considered to have potential to become one of the league's best defenders.[13]
Sicily had another good season in 2019, being selected in the extended All-Australian squad for that year, the only Hawthorn player to do so.[14] He was considered especially important to Hawthorn's defence.[15] At the end of the season, he re-signed with the club till at least the year 2022.[16]
Sicily missed the 2021 season as he was recovering from a ACL injury sustained during the 2020 season.
On 16 May 2022, Sicily announced that he had agreed to a 5-year contract extension with Hawthorn, tying him to the club until at least the end of 2027.[17]
In February 2023, Sicily was appointed the 38th captain of Hawthorn, with the 28-year-old succeeding the retired Ben McEvoy who served in the role for two seasons.[18]
In Round 11 2023, Sicily had a career high 43 disposals against St Kilda in Hawthorns 10 point win.
On-field temperament
Sicily is widely regarded and known for having a short temper, something he himself has acknowledged.[19]
^The 2020 season was played with 17 home-and-away matches per team (down from 22) and 16-minute quarters with time on (down from 20-minute quarters with time on) due to the impact of the COVID-19 pandemic.