With Cardiff losing 1–0, Earnshaw scored a bicycle kick from ten yards out following a cross by John Williams to earn his side a point. However, after appearing in three further matches during the opening month of the season, he spent time away from Cardiff to attend trials with Middlesbrough under Bryan Robson and Fulham under Kevin Keegan. He returned to Cardiff but struggled to break into the side under manager Frank Burrows with Earnshaw later stating that he believed Burrows thought he would not "make the grade." After making a single appearance at the start of the 1999–2000 season, Earnshaw was loaned to Scottish side Greenock Morton in January 2000 by Burrows to gain experience and "toughen up", living above a local pub. Earnshaw later admitted that the experience at Morton helped him, commenting "It made me realise that I needed to work hard at my game so I could show Cardiff City that I could become a good player." During his loan spell, he played three games in the Scottish Football League First Division, scoring twice, and one Scottish Cup tie against Rangers. Originally signing on an initial three-month loan deal, he was recalled by Cardiff manager Billy Ayre after just one month when he replaced Burrows in charge and made five appearances in the final three months of the season, scoring once in a 2–1 defeat to A.F.C. Bournemouth. The following season proved to be a breakout year for Earnshaw as he established himself in the first team, scoring 25 goals in all competitions including hat-tricks in a league match against Torquay United and a third round FA Cup tie against Bristol Rovers. His form saw him receive Cardiff's Young Player of the Year award and saw him named in the Football League Third Division PFA Team of the Year. In the 2002–03 season, Earnshaw scored on the opening day of the season in a 2–1 victory over Oldham Athletic but was used largely as a substitute in the opening month after manager Lennie Lawrence opted to play Andy Campbell after Earnshaw failed to score in pre-season. However, on 11 September 2002 he was handed a start against Boston United in the League Cup and scored a hat-trick. He went on to enjoy a prolific season, scoring two further hat-tricks in matches against Queens Park Rangers and Tranmere Rovers and also scored six braces, as Cardiff won promotion to the First Division after defeating Queens Park Rangers in the 2003 Football League Second Division play-off Final at the Millennium Stadium.