The 1998–1999 season saw Leeds United competing in the FA Premier League (known as the FA Carling Premiership for sponsorship reasons), and the UEFA Cup.
Leeds were expected to progress once more under manager George Graham after the former Arsenal manager guided Leeds to 5th place in his first full season in charge. Graham had added to his squad, signing defender Danny Granville and Dutch striker Clyde Winjard. After just 4 games Leeds went to top of the Premier League for the first time in their history. But rumours began to spread of George Graham taking the Tottenham job after Spurs had sacked Christian Gross, the saga dragged on when finally after a UEFA cup game against Maritimo of Portugal, Graham indeed left Leeds for Tottenham. Graham's assistant David O'Leary took charge as Leeds attempted to court Leicester boss Martin O'Neil, who eventually refused. But United's performances on the pitch began improving -despite only drawing several games, many teenage players were given debuts by O'Leary and put in great performances, such as the game against Italian giants Roma in the UEFA cup (although Leeds were knocked out). Needless to say, O'Leary was appointed manager in time for the game against Derby which ended 2–2. Leeds then began winning regularly, playing impressive attacking football. They had several talented youngsters, including goal keeper Paul Robinson, defenders Ian Harte and Johnathan Woodgate, mid fielders Lee Bowyer (who was signed from Charlton 2 seasons before) and Stephen McPhail, as well as strikers Alan Smith and Harry Kewell. But David O'Leary was eager to bring in experienced players to add to this young team, and signed David Batty from Newcastle. Batty was a key player in the Leeds side that won the old Division 1 title in 1992 and a fan favourite. In the run up to Christmas, Leeds were almost in contention for a shot at the title, but suffered back to back losses against Southampton and Newcastle in the new year. This ended any league-winning hopes, and they were also knocked out of the FA cup. Despite this, Leeds ended the season in red hot form, setting a record of 7 straight wins and a 1–0 victory over Arsenal, costing the gunners the title race. Leeds finished an impressive 4th place in the league – their highest finish yet. With this achievement, and with one of the most exiting young squads in the country, the future certainly looked bright for United.
^McPhail was born in Westminster, England, but was raised in Dublin and would make his international debut for Ireland in May 2000.
^Gray was born in Harrogate, England, but also qualified to represent Scotland internationally and would make his international debut for Scotland in April 2003.