In 1999, they continued on this upward trajectory, finishing fifth, as well as making the semi-finals of both the Challenge Cup and the Grand Final play-offs. This became one of the most famous seasons in the clubs recent past, with fans still remembering it with reverence. The team included many home grown players such as current assistant Danny Orr, and included that years Man of Steel winner Adrian Vowles. In 2000, the rise seemed to stall, as they repeated their fifth-place ranking and made the play-offs for a consecutive season. Raper left Castleford midway through the 2001 campaign to take charge of Wigan, his assistant Graham Steadman took over the reins as head coach.