The 1899–1900 Football League season was Small Heath Football Club's eighth in the Football League and their sixth in the Second Division. They spent most of the season in the top four in the 18-team division, but rarely in the top two, eventually finishing in third place, six points behind the promotion positions. They also took part in the 1899–1900 FA Cup, entering at the third qualifying round and losing to Walsall after a replay in the fifth qualifying round. In local cup competitions, they were beaten by Wolverhampton Wanderers in the first round of both the Birmingham and Staffordshire Cups, and by Walsall in the semi-final of the Lord Mayor of Birmingham's Charity Cup.

Twenty-one players represented the club in nationally organised first-team competition, and there were fifteen different goalscorers. Bob McRoberts was the top scorer with 24 goals, of which 19 came in league matches. No other player reached double figures. McRoberts, goalkeeper Nat Robinson and full-back Arthur Archer played in every match. Off the field, the club made a significant financial loss over the season. The directors made it clear they could not continue funding a loss-making enterprise, and suggested that a reduction in players' wages was the only course of action.

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. They scored more goals than any other team in the division except Manchester City, and scored more at home than any other, but their away record was poor. The Dart suggested that "the backs are all right, the defect that needs remedying is the half-back line, which is hardly up to the necessary standard."Walter Abbott, who had scored 42 goals (34 in the league), both totals remaining (as of 2014^[update]) club records, signed for Everton for a fee of £250 plus the proceeds of a midweek friendly match.William Robertson left for Bristol Rovers, and Clutterbuck joined Southern League club Queens Park Rangers.Walter Main, a forward signed from Airdrieonians, was "expected to be a worthy successor to Abbott", and half-back Tom Farnall returned from Bristol Rovers.

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