 He made his debut in a Football League Division One against Sheffield Wednesday on 11 April 1898, scoring his first goal in the same match.The winger had a very successful time at Anfield missing just a single game in his first 2 seasons at the club, he even bagged a very respectable 19 goals, not bad for someone playing out on the flank.Robertson was an ever present in the 1900–01 season as the Reds went on to win their first league title.