In October 2020, Wilkie made his debut for Dundee in a Scottish League Cup group stage match against Cove Rangers, coming off the bench late on in a 3–0 win.[3]
In June 2021, Wilkie signed his first professional contract with Dundee.[4] In August, Wilkie joined Midlands League side East Craigie on loan. He scored his first goal for the Shipbuilders in a Scottish Junior Cup match against Banchory St Ternan, and would be named Man of the Match in the 7–2 win.[5] In May 2022, Wilkie signed an extension with Dundee which would keep him there for another season.[6]
In Dundee's opening competitive fixture of the 2022–23 season, Wilkie would appear as a substitute in a Scottish League Cup win over Hamilton Academical.[7] On 13 August 2022, Wilkie would join Scottish League One side Peterhead on loan.[8] Wilkie made his debut the same day away to Falkirk.[9] Wilkie would grab his first goal for the Blue Toon on 25 February 2023, equalising to help Peterhead clinch a point against Kelty Hearts.[10] Despite Peterhead being relegated at season's end, Wilkie was named as the club's Young Player of the Year Award winner.[11]
On 4 August 2023, Wilkie joined Scottish League One club Edinburgh City on a season-long loan.[12] The following day, Wilkie made his debut for the Citizens as an early substitution in a league game away to Stirling Albion.[13] Wilkie scored his first Edinburgh City goal on 7 October against Kelty Hearts.[14] After struggling with injury during his loan stint, Wilkie was recalled by Dundee on 18 January 2024.[15]
On 9 February 2024, having played for two senior SFA clubs already in the season, Wilkie joined Midlands League club and SJFA member Broughty Athletic on loan until the end of the season.[16][17] Wilkie made his debut the following day, starting in a 10–0 league win away to Brechin Victoria.[18] On 20 May, Dundee confirmed that Wilkie would leave at the expiry of his contract.[19]
On 28 May 2024, Wilkie joined Scottish League One club Arbroath.[20] He made his competitive debut on 16 July in a defeat against his former club Dundee in the Scottish League Cup group stage.[21] On 28 September, Wilkie scored his first goal for the Red Lichties in an away league victory over Cove Rangers.[22]