United played their first competitive game against Notts. Rangers FC, of the Midland Counties League, on 7 September 1889, losing 4–1 at Meadow Lane; W. Robertson from Dundee, scored United’s first ever competitive goal. Following this game Heeley FC was chosen to be the first Sheffield opponents and this match was played on the Sheaf House ground. United won 2-1, the two goals coming from James Duncan and S. Mack and the game was watched by 2,200 spectators. The first ever United match at Bramall Lane on the 28th September against Birmingham St. George FC, ended badly with a 4-0 defeat, watched by 4,000 spectators.
(There is much more detail on United’s early history in my newly released book A History of Sheffield Football 1857-1889: Speed, Science and Bottom http://bit.ly/2qYw0r0 )
Because United did not belong to a specific league in 1889 the vast majority of the games were friendlies, but they did enter the FA Cup and after navigating four qualifying rounds against Scarborough FC, Heeley FC, Sheffield FC, and Rotherham Town they met and beat Burnley FC in the first round. The second-round match away at Bolton Wanderers FC represents United’s darkest ever day when they experienced their worst ever defeat by thirteen goals to nil on 1st February 1890. The initial draw had been for a home tie at Bramall Lane but the United committee took ‘£40 or £50’ to switch the match to Lancashire. With United playing the Trotters next Tuesday an away win could help make recompense for this ancient black mark.
According to Denis Clarebrough and Andrew Kirkham’s book- ‘Sheffield United Who’s Who’, Howlett, the United goalkeeper who had poor eyesight, lost his glasses early on in the game and spent much of the match searching for them in the muddy goal mouth. Charlie Howlett from Gainsborough Trinity FC was one of five local professionals, who answered United’s advert placed when the club was formed in March 1889:
“Sheffield United Cricket Club. The committee have decided to form a FOOTBALL CLUB for next season, for Bramall Lane ground. Professionals may send testimonials and on or before, March 30th to Mr. J.B. Wostinholme, 10 Norfolk Row.”
Charlie Howlett stayed with United for five seasons until he returned to his previous club Gainsborough Trinity FC, where he played for another nine seasons before retiring.
They had much greater success in the Sheffield FA Challenge Cup making the final in their first season without conceeding a single goal against Exchange FC, Heeley FC, Attercliffe FC and Staveley FC in the early rounds. They played Rotherham Town in the final at Bramall Lane in a match that ended in a goaless draw and United eventually lost by a single goal in the replay played at The Holmes, Rotherham.