Daniel (Dan) Bailey was born in East Ham on 26th June 1893. He played local football before being signed by West Ham United in 1912. Syd King saw Bailey as a replacement to Danny Shea who he sold to Blackburn Rovers in January 1913.
Bailey made his debut against Northampton Town on 15th March 1913. He joined a team that included Fred Harrison, Herbert Ashton, Syd Puddefoot, George Hilsdon, Jack Casey, Fred Blackburn, Albert Denyer and Tommy Randall. He scored his first goal for the club against Millwall on 5th April 1913. West Ham finished in 3rd place that season but Bailey was far from an ideal replacement for Danny Shea scoring just two goals in 10 games (Shea had scored 15 in 22 before he left the club).
After failing to score in the first two games of the 1913-14 season Bailey was dropped from the first-team. He regained his place in the game against Exeter City on 23rd December 1913. He scored in West Ham's 6-1 victory over Bristol Rovers on 3rd January 1914.
West Ham began a good run of form in January 1913 and a team that included Bailey, George Hilsdon, Fred Harrison, George Butcher, Herbert Ashton, Albert Denyer, and Jack Casey went through the rest of the season unbeaten. This included 7 games won and 8 games drawn. That season Bailey scored 9 cup and league goals in 23 games.
Despite the outbreak of the First World War the Football League decided to allow the 1914-15 season to continue. West Ham United had high hopes that they could win the Southern League for the first time. In Syd Puddefoot they had the country's most promising young goalscorer.
West Ham won six of their first 12 games. Syd Puddefoot got nine goals in these 12 games. George Hilsdon and Richard Leafe were also in good form and got 7 between them. Once again West Ham were challenging for the Southern League title. Bailey started in the first-team but he was only able to score 5 goals in 20 games and was eventually dropped in December, 1914.
Attendances at league games fell dramatically during the second-half of the season because of the impact of the First World War. It was decided that the Football League would not operate in the 1915-16 season. As football players only had contracts to play for one season at a time, they were now out of work. It has been estimated that around 2,000 of Britain's 5,000 professional footballers now joined the armed forces. This included Dan Bailey who served in Egypt during the war.
Bailey returned to the West Ham United team after the war and played alongside Syd Puddefoot and George Butcher in the 1919-20 season scoring nine goals in 27 games. Bailey moved to Charlton Athletic in 1921 and scored 8 in 33 before moving on to Clapton Orient in 1922. He finished his career at Margate.
Dan Bailey died aged 74 in April 1967.