W. Hart and Albright and Wilson's enabled Hart to influence Wheldon's father favourably towards his club. Signed initially on amateur forms, he made his debut on 15 February 1890, scored twice in a 6–2 defeat of Darwen, and gave Football Notes no reason to moderate their view of him as "a young player who one day will be one of the forwards of whom the district is most proud", "a born footballer [who] cannot fail to come on apace". He played once more for the first team in what remained of that season, and then turned professional. He was ever-present during the 1890–91 season, with eight goals from the 22 Alliance matches and a hat-trick against Hednesford Town in the FA Cup. Again ever-present for Small Heath in the final season of the Alliance, his 21 goals from 22 matches helped the team finish third. The club's application for election to the Football League First Division when it was expanded to 16 clubs was unsuccessful, but it was among 12 clubs, mostly from the Alliance, elected to the newly formed Second Division. Wheldon's and Small Heath's first Football League goal opened the scoring in a 5–1 win against Burslem Port Vale, and he went on to score 25 goals from the 22 matches, finishing the season as top scorer in the division. The team finished top of the table, a point ahead of Sheffield United, but promotion was not automatic even for champions; they had to play a test match at a neutral venue against the First Division's bottom club, Newton Heath. Wheldon scored the equaliser and "all but scored a second" in a 1–1 draw at Stoke's Victoria Ground; in the replay, Frank Mobley put Small Heath 1–0 up and Wheldon hit a post before Newton Heath won 5–2. Wheldon's 22 league goals helped Small Heath finish as runners-up to Liverpool in 1893–94. The test match, again at Stoke, was level at 1–1 against Darwen until late goals from Billy Walton and Wheldon secured the victory and with it promotion. In October 1894, Small Heath played West Bromwich Albion in a benefit match for Wheldon; his left-wing partner, Tommy Hands, and a triallist goalkeeper were both injured during the game, and only 2000 supporters were present. A few days later, he scored with the first penalty kick awarded to Small Heath, at home to local rivals Aston Villa, one