While attending Harris Academy, Wighton was snapped by Dundee under the management of Barry Smith, the team he supported as a boy.
[1] He came through the same training clinic, run by Ian Cathro, as fellow Scottish prospects Ryan Gauld and John Souttar.
[3] Manager John Brown said in March 2013 that if Wighton continued his form at youth level he could soon make the first team, which could have meant him becoming the club's youngest-ever first-team player.
[7] In the 2013–14 season, Wighton made his debut for the club, coming on as a substitute for Craig Beattie in the 81st minute, as Dundee beat Cowdenbeath 2–0 on 5 October 2013.
[10] He became the youngest-ever scorer in a competitive game for Dundee at the age of 16 years, three months and 13 days on 9 November 2013, beating the record held by Jocky Scott, scoring a goal in a 2–0 win against Raith Rovers.
[14][15] At the end of the 2013–14 season, the club's manager Paul Hartley said he may consider loaning out Wighton to gain first team experience with the hope he could "do a Stevie May," the striker who Hartley had on loan at Alloa Athletic from St Johnstone in 2011–12 and had gone on to be a first team regular in the Scottish Premiership, earning a move to Sheffield Wednesday.
On 23 June 2015, after much speculation it was finally confirmed that Wighton had joined Raith Rovers on a six-month loan deal.
[22] Wighton managed to add 2 goals to his name after returning to the club from his loan spell, he came off the bench to score in an empathic 5-2 Victory over Ross County and more noticeably he scored a 93rd minute winning goal in a Dundee derby known as the "Doon Derby", a result which confirmed that rivals Dundee United would be relegated.
After impressing manager Neil McCann in pre-season, Wighton picked up a knee ligament injury which ruled him out for several months.
[34] The next day, Wighton would score a brace in a 5–0 rout of Queen of the South at East End Park which officially confirmed Dunfermline as Scottish League One champions.