At the time there were several other talented youngsters in the team including Kelly Houlker, Bob Crompton, Tom Booth, Sam McClure, Tommy Briercliffe, Arnie Whittaker and Fred Blackburn. The team also included experienced players such as George Anderson and Tom Brandon.
Blackburn found itself in an relegation struggle in the 1899-1900 season. The club had to win one of its last two games against Notts County and Preston North End in order to avoid the drop to the Second Division. Blackburn lost to Preston but managed to beat Notts County 2-0. The Blackburn Times criticised the performance of the Blackburn team arguing: "There can be no such thing as standing still in the football world as in many other things, and as the Rovers have not made headway they must have been going backwards. Alas, this is only too plain. The rovers of today are not the Rovers of yore, when their fame spread far and wide".
The following season, two of Blackburn's most experienced players, George Anderson and Tom Brandon, left the club. Tom Booth, an English international, was sold to Everton and Tommy Briercliffe moved to Stalybridge Celtic. Considering the loss of these good players, Blackburn did well to finish in 9th place. Blackburn also won the Lancashire Cup beating Burnley 4-0 in the final. That season Arnie Whittaker was top scorer with 8 goals.
The 1901-02 season saw a major improvement in the form of Blackburn Rovers. For a while it looked like they would win the First Division title. However, Sunderland beat them 1-0 at Ewood Park and this started a poor run that left them in fourth place by the end of the season. The form of Whittaker was outstanding.
The 1902-03 season was once again a relegation struggle. Joseph Walmsley, the manager, bought Adam Bowman from Everton in March, 1903. The following month Bowman scored a couple of goals against his former club in a 3-0 victory. Four days later, Bowman scored another two goals against Newcastle United. These two results meant that Grimsby Town, rather than Blackburn was relegated from the First Division of the Football League.
Rumours began to circulate that Blackburn Rovers had bribed Everton players to lose the game. Officials at Grimsby lodged an official protest and the Football Association ordered an inquiry was held into the game. A report by the FA claimed that there was evidence that Joseph Walmsley had tried to arrange a win for Blackburn Rovers. However, they believed that Everton players had not taking any bribes and that the final league placings should remain unaltered. Walmsley was immediately banned from having any further involvement with football.
In July 1903, Robert Middleton, a former school teacher, was appointed as Blackburn's new secretary/manager. Middleton purchased Bob Evans, a Welsh international goalkeeper, from Wrexham for £150. In November, 1903, Middleton also persuaded Fred Pentland, a regular goalscorer for Blackpool, to join the club. Pentland scored seven goals in 18 league appearances, but his efforts could not stop Blackburn from being involved in another relegation struggle. The club eventually finished in 15th place in the league.
It was the same story the following season. Despite good individual performances from Arnie Whittaker, Bob Crompton, Adam Bowman, Bob Evans, Fred Blackburn and Fred Pentland, Blackburn could only finish in 13th place. In an article that appeared in the Blackburn Times a journalist wrote: "Like its two predecessors, the season of 1904-05 has been one of disgrace to the Rovers". Blackburn failed to improve during the next two seasons and in 1907 Whittaker was transferred to Accrington Stanley. In the eight years he was at the club, Whittaker had scored 57 goals in 250 games.