Geddington, Northamptonshire born centre half Herbert Dainty started his playing career with local Midland League club Kettering as an amateur in 1897 and is first recorded playing “senior” football for them when he took part in an FA Cup tie against Loughborough in November 1898.
He joined Second Division Leicester Fosse in August 1899 and made his Football League debut for them at Luton Town in September 1899, scoring 3 goals in 34 appearances before in May 1900, he moved to fellow Second Division team New Brighton Tower. At the end of the 1900-01, despite finishing in a creditable fourth place, New Brighton Tower folded and Dainty returned to Leicester Fosse after 3 goals in 35 appearances. In his second 24 game spell at Leicester Fosse, one of his team-mates was Charles Webb who was later to play with him at Southampton (1904-1905) and Dundee (1905-1911).
He moved on again at the end of the season joining Southern League Northampton Town for the 1902-03 season. His transient career continued when he joined Notts County in May 1903 season to play in the First Division for the first time, making 21 appearances in 1903-04. In May 1904, Dainty decided to move South to join Southern League champions Southampton. According to Holley & Chalk’s The Alphabet of the Saints, Dainty was “a worthy successor to previous Saints’ centre-halves, Bowman and Chadwick. Bert was coolness personified and was at his best during desperate pressure around the goal area.” He played alongside Saints’ stalwarts, Samuel Meston and Bert Lee as Saints failed to repeat their previous season’s performance, finishing in third place. At the end of the season Dainty decided to move on again, which “provoked an outcry in the town” after a single goal in 31 appearances.
He moved this time to Scotland where he joined Dundee in May 1905. Dundee was obviously to his liking as he stayed at Dens Park for six seasons, scoring 24 goals in 187 appearances, and he was one of four Englishmen who helped Dundee to win the Scottish Cup in 1910 when they beat Clyde 2-1 in the Final at Ibrox. He also played for The Scottish League in October 1910 against The Southern League at Millwall.
He returned to England in May 1911 with Second Division Bradford Park Avenue and stayed just over two seasons in Bradford scoring once in 71 appearances before returning to Scotland to join Ayr United in the autumn of 1913 as player manager. He continued in that role until April 1915 when he joined Dundee Hibernian (now United) as player manager becoming the club’s second ever manager, a role he relinquished in 1917. and retired from playing the following year, staying at the club as secretary and then briefly in 1922 as chairman. During the First World War, Dainty stayed on Tayside, where he formed his own side known as “Dainty’s XI” utilising footballers who were stationed in Tayside and Fife during the War which played regular matches against other Tayside teams raising money for wartime charities. This led to him standing down as Dundee Hibs manager, although he stayed on as a player until the end of the 1917/18 season.
In 1920 he joined the board at Tannadice, and became Club Chairman in 1922. After leaving Dundee Hibernian, Dainty travelled to South America as a coach, before returning to England as manager of Kettering Town from 1931 to 1932 and as a coach with Ipswich Town from 1932 to 1934.