Despite Michael Owen's brilliant form, Liverpool were unable to mount anything like a title challenge and seemed to be a side in transition following the appointment of their new head coach and adapting to a new style, which saw new signing Rigobert Song arrive and the likes of Jason McAteer and Rob Jones leave, along with the club's longest serving player Steve Harkness, who joined Benfica on 7 March 1999 after almost ten years at Anfield.

September began with a 2–0 win over Coventry City which saw the Reds top the table after four matches, level on points with Aston Villa, while title favourites Arsenal and Manchester United were fifth and ninth respectively.

Manchester United were now one point off the top, while Arsenal had re-emerged as contenders for the title they had won the previous season, now occupying third place.

[3] There was positive news on the European scene that late autumn as they edged past Valencia on away goals in the UEFA Cup second round.

However, the month ended on a higher note as wins over Aston Villa and Blackburn Rovers lifted them back up to eighth place.

[4] Liverpool's dreams of European glory were ended on 8 December 1998 when they suffered a hefty defeat to Celta Vigo in the UEFA Cup third round.

However, their hopes of glory ended in the fourth round when they surrendered a 1–0 lead in the dying minutes to lose 2–1 to Manchester United at Old Trafford.

[7] Spring brought a similar pattern of results, and by 21 April, they had slid down to tenth place in the league with even their UEFA Cup qualification hopes looking slim.