He played seven games for the Dandenong Stingrays in the 2010 TAC Cup, averaging 30 disposals, kicking six goals and leading the league in contested possessions with 13 per match. At the end of this season he was signed by GWS Giants as underage selection. He spent 2011 playing for the Giants in the NEAFL one year prior to their AFL entry.
Greater Western Sydney
Shiel played 135 games at Greater Western Sydney in seven seasons, playing mostly as one of the key midfielders in the side. He achieved All Australian selection in the 2017 season. At the conclusion of the 2018 AFL Season, Shiel was traded to Essendon.
Essendon
Following a salary cap issue at the GWS Giants,[3] Shiel was encouraged to explore his options elsewhere and with the intention to continue his football in Victoria in the coming years, he decided to entertain the idea.[4] He met with four clubs: St Kilda, Hawthorn, Carlton and Essendon and decided with the latter, Carlton explored extreme methods in trying to lure Dylan, flying the midfield star to Noosa on a private jet as part of a bold pitch to snare his signature. It is believed he turned down more than $3 million to sign with Essendon as he was chasing success over money and was put off by Carlton’s luxurious pitch which included caviar and an entourage of Carlton power brokers, including Chris Judd.[5][6] The trade was done in the dying minutes of the 2018 Trade Period with Essendon sending Pick 9 and their 2019 first-round pick to GWS, and GWS' 2019 second-round pick being sent back to Essendon along with Shiel.[7]
Shiel commenced his first pre-season at Essendon in November 2018 with the expectation of slotting straight into the starting midfield in his first game for the club against his old side on 24/3/2019.
After a full preseason, Shiel played 4 games adjusting to playing in the Essendon midfield until playing his "breakout game" at his new club in Round 5 against North Melbourne. Regarded by many as best afield, Shiel recorded an astonishing 866 metres gained together with his 10 inside 50s and 4 goal assists. In the 2019 season Shiel came second in the Essendon Football Club Best and Fairest.
^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.
