Wilsontown, Carnwath, Lanarkshire born full back (he could play both sides) Archie Annan began his football career with West Calder Swifts in August 1899 before joining Scottish League club St Bernard’s in 1900. He had two seasons with the Edinburgh club before being signed by First Division Sunderland in April 1902, making his Football League debut in 2-1 win over Notts County in April 1903, his only appearance for The Wearsiders. In January 1904 Sheffield United signed him, and he made 9 first team appearances for The Blades before the end of the season deputising for Harry Thickitt and Peter Boyle, and a further 19 in their 1904-05 campaign as they finished 6th in the League Championship.
Annan followed newly appointed Bristol City manager Harry Thickitt to Ashton Gate for £200 in April 1905. Annan was ever present with 38 League appearances at right back as Bristol City finished as Second Division Champions in 1905-06, and formed a notable defensive full back partnership with Joe Cottle. Ever present again for a second successive season in 1906-07, City finished the campaign as runners up in the League Championship, their highest ever League position. Annan played just 15 matches in 1907-08 as new signing Bob Young was preferred at right back, but in 1908-09, Annan replaced Young as the regular right back, making 26 League appearances and playing in all 10 FA Cup ties, including the 1909 FA Cup Final which City lost 1-0 to Manchester United at The Crystal Palace, still the club’s only FA Cup Final appearance.
He made a further 31 appearances in 1909-10, and was again replaced by Bob Young in the later stages of the season. Annan did not feature at all in the City team in the 1910-11 season, as Bristol City were relegated back to the Second Division. The final League match of the season, a 1-0 defeat to Everton on 29th April 1911, was awarded as a joint benefit for Arthur Spear and Archie Annan, although neither played in the game.
After 161 appearances for Bristol City, Annan moved onto Burslem Port Vale in July 1911. He made his debut at the Athletic Ground in a 1-0 win over Oldham Athletic Reserves on 4th September, but injured himself in a match against Crewe Alexandra twelve days later. He failed to hold onto his first team place upon his recovery, and was released at the end of the 1911-12 season, after picking up a Central League runners-up medal. Annan was then appointed manager of Welsh Southern League club Mid Rhondda in July 1911, where he was assisted by former Bristol City colleagues Joe Cottle and Bill Demmery. He subsequently returned to Bristol City in March 1921 and spent five years as coach at the club.