Steven Gerrard made his Liverpool first-team debut on 29 November 1998 against Blackburn Rovers when he came on as a last minute substitute for Vegard Heggem. He went on to make thirteen appearances in his debut season. In the next season, 1999-2000, Gerrard played alongside Jamie Redknapp in central midfield for much of that campaign.
Two firsts for Gerrard that season - his first senior goal and his first red card. The red card came against Everton in the derby at Anfield for a late foul on Everton's Kevin Campbell. His first goal came later that season in a 4–1 victory over Sheffield Wednesday. His slalom run from midfield ending in a low shot buried in the left hand corner of the Anfield Road net. The 2000–01 season was not only memorable for Steven Gerrard himself but also for the club overall.
Gerrard himself made fifty starts in all competitions and scored ten goals as Liverpool won the League Cup, FA Cup, and the 2001 UEFA Cup. Another step forward in Gerrard's progression came in October 2003 when he replaced Sami Hyypiä as Liverpool captain. The end of the 2003/04 season saw a big change for Liverpool and nearly a big change for Steven Gerrard himself.
Gerard Houllier quit after a disappointing 2003–04 campaign, and Gerrard was linked with a transfer to Chelsea during the close season. He evidently wasn't happy with the lack of progress being made at the club but after much soul searching Gerrard turned down an alleged £20 million offer from Chelsea to stay with Liverpool and work under new manager Rafael Benítez.