[2][3] He played one year at Prince Andrew High School in his native Dartmouth, Nova Scotia for Coach Ken Cooper [4] before moving to the United States to join Oak Hill Academy in Mouth of Wilson, Virginia at the age of 15.

[8] Representing the World Select Team, Wigginton saw 22:16 minutes of action at the 2017 Nike Hoop Summit, scoring eleven points and handing out a team-high seven assists.

[11] In his sophomore season, he averaged 13.4 points, four rebounds and 2.1 assists in 26 minutes per game and was named the Big 12 Conference Sixth Man of the Year.

[18] On May 18, 2020, Wigginton signed with Ironi Nes Ziona of the Israeli Premier League[19] where he averaged 8.6 points while shooting .550 from the field.

[22] On April 10, Wigginton scored 18 points and recorded 8 assists during Milwaukee's final regular season game, a loss to the Cleveland Cavaliers.

In his Summer League debut for the Bucks, Wigginton scored seventeen points and seven assists in a 94–90 win over the Brooklyn Nets.

He missed the quarter and semi final due to concussive symptoms,[33] but was back for the championship game against Italy, scoring eleven points while tallying three rebounds and three assists.