After being close to the second promotion place throughout the 1898–99 season, Small Heath eventually finished eighth, five points behind second-placed Glossop North End and a further six behind champions Manchester City.

"[2] Walter Abbott, who had scored 42 goals (34 in the league), both totals remaining (as of 2020[update]) club records,[a] signed for Everton for a fee of £250 plus the proceeds of a midweek friendly match.

[12] Playing with the wind, Small Heath took an early lead, Wigmore hooking the ball into the net, and the same player scored the third goal off the crossbar in the second half as his side won 3–2.

Playing against a strong wind, McRoberts opened the scoring when he was first to the rebound after his shot was fumbled, and Bennett converted a cross from Sid Wharton not long before the interval.

Freddie Fenton pulled one back with a header after Robinson missed his punch, and Bennett made the final score 4–1 after the goalkeeper failed to hold a low shot.

At home to Bolton Wanderers, relegated from the First Division in 1899, the defence was worked hard from the outset, but Small Heath "began to wake up", and the attack went to the other end, John Willie Sutcliffe playing "grandly", particularly when the visitors temporarily went down to ten men.

[1] McRoberts and Wigmore scored in the first half, against the wind, and the same players contributed three goals in the second to give Small Heath an easy victory at home to Lincoln City.

On a fine day on a pitch in good condition, Small Heath fielded a stronger eleven than had recently been the case, Alex Leake resuming at centre-half.

[27] A crowd of more than 13,000 spectators attended league leaders Small Heath's visit to Sheffield Wednesday, where the kickoff was delayed for ten minutes because the referee had not arrived.

[29] Oswestry United agreed to switch the venue of the third qualifying round of the FA Cup to Coventry Road, took an unexpected but, on the balance of play, deserved 2–1 lead in the first half, and then conceded nine without reply.

[32] The second was the 33-year-old full-back Bob Cain, who played for many years for Sheffield United without missing a league match,[31] and left Tottenham Hotspur for Albion Rovers the previous season because "the hard work was too much for him.

Scriven opened the scoring for the visitors with a header just after Main had a goal disallowed for offside, and Leake doubled the lead just before half time with a shot that gave the goalkeeper no chance.

[38] As the attendance was expected to be augmented by Aston Villa supporters unable to go to Liverpool to watch their own team, Small Heath arranged for half-time and full-time scores from Anfield to be displayed at their ground.

In the second half, the Heathens added three more goals and had another three disallowed, all for offside; the referee "was very strong on the off-side rule, and some of his decisions, which affected both sides, greatly displeased the spectators".

[43] After frozen snow was removed from the playing surface, Small Heath enjoyed a deserved 3–0 victory against Luton Town with two goals from Bennett and a late third from Scriven.

The Birmingham Post attributed Walsall's dominance to centre-half Caesar Jenkyns – Small Heath's former captain – "who again played a wonderfully-fine game—not only checking the opposing vanguard but feeding his own forwards with excellent judgment.

[1] The "miserable weather" left the pitch in a "sloppy" condition and deterred the paying public from witnessing Small Heath's 5–0 defeat of Middlesbrough with goals from five different scorers: Pratt, Bayley and Bennett in the first half, Scrivens and McRoberts in the second.

[49] In the postponed Birmingham Cup-tie, Wolverhampton Wanderers missed a second-half penalty awarded when Lester, selected at full back in place of Archer, caught the ball in the mistaken belief that it had gone out of play, but scored the only goal of the game five minutes later.

The defence and half-backs, particularly Leake at centre half, "times out of number breaking up the attack of his opponents by his dogged determination", were singled out for praise, but the forwards were "ragged and unsatisfactory", not helped by Scrivens' shoulder injury.

[52] After Gainsborough Trinity took the lead at Coventry Road, Small Heath lost a forward when Jack Aston, newly arrived from Woolwich Arsenal, suffered a coughing fit and was withdrawn on doctor's orders.

[56] On hard ground, with snow carried on the "biting cold wind", Alec Leake, playing at inside-left instead of his customary half-back position, was involved in most of the six goals Small Heath put past Loughborough to move up to second place in the division.

[57] Against Grimsby Town in the match originally postponed because of fog, the home side's "failure to score was simply unaccountable", while Pratt's attempted clearance produced an own goal to give the visitors an unexpected victory.

Heavy rain had left the pitch muddy with pools of standing water, but the referee made little allowance for the conditions, stopping the game frequently, "often for trivial breaches of the law".

Still without McRoberts, the team's weakness was in attack – Billy Walton was the fifth different centre-forward in five games, and less effective than Scrivens – and at left-half, where Layton was frequently beaten, and Grimsby won by two goals to one.

The Glasgow Herald thought the English half backs, "while all working hard, showed no special aptitude such as is necessary for great matches", and the Birmingham Daily Post believed that having to desert his "dashing, bustling" style for a more "quiet, scientific" method of play affected him adversely.

[81] In a post-season friendly, Jack Aston's goal earned a draw with West Bromwich Albion,[82] and in the last match of the season at Coventry Road, the reserves played a Birmingham Police team to benefit the Association for Providing Boots and Clothing for Destitute Children.

The Liverpool Mercury thought that "Small Heath deserve some commiseration, for they rank a good third, but next season the probability is that they will not have such strong rivals to battle against as the Wanderers and the Blades".

[84] The Sheffield Independent concurred,[85] but the Dart was less supportive: "The Heathens were confidently expected to gain second place, but they gave one or two woeful exhibitions at home, and threw good chances away.

Chairman W.W. Hart, who was re-elected to the management committee of the Football League at its annual meeting in May,[87] reported that the club had made a significant financial loss over the season.

[85] The Dart took a positive view: "The Heathens mean making a great attempt to gain admission into the 'charmed circle' this season, and if they will only perform a little more consistently away from home I think they will just about accomplish the feat.