Cole was United's second top scorer again in 1999–2000 with 19 goals in 28 Premier League matches. He collected his fourth Premier League title medal in five seasons, and scored over 20 goals in all competitions for the third successive season. Cole scored many goals for United including the only goal of the game in their top-of-the-table clash against their closest rivals Leeds United. He also joined an elite group during this season by scoring his 100th goal for the club in a 2–2 draw against Wimbledon.