In January 1999, Pringle signed for Premier League outfit Charlton Athletic on a two-month loan from Benfica. Under the stewardship of Alan Curbishley, the club was embroiled in a relegation battle and had added Pringle to bolster the club's attacking ranks which included the likes of Clive Mendonca, Andy Hunt, Kevin Lisbie and Bradley Allen. He was handed his debut on 9 January 1999 in the club's 1–3 away defeat against Southampton when he replaced Steve Jones in the 71st minute.