However, he made an excellent start to the new century by riding his first winner on the Duke of Portland’s Serio Comic, trained by Lambton, in the Apprentices’ Maiden Stakes at Lincoln on March 27, 1900. Two more wins in apprentice races followed before he gained his first success against senior jockeys when Weybridge won the Thames Handicap at Windsor on July 28. The winning margin was two lengths, the runner-up being ridden by future champion jockey Willie Lane.