Dickie was born in Dumbarton, and started his football career with Dumbarton Episcopalians, Dumbarton Union and Methlan Park, before joining Dumbarton F.C. in 1890.
Dumbarton were an amateur team at that time, and he was employed as a draughtsman in the local shipyards.
Nottingham Forest were the first English club to show interest in signing him. They were followed by Liverpool. However, it was Everton that gained his signature in 1882, and shortly after his arrival in Liverpool he was to play in the first game at Goodison Park, an “exhibition match” against Bolton Wanderers. He had a long and distinguished career with the Toffee’s, becoming club captain in 1895.
In 1902, as his playing career on merseyside was winding down, Dickie applied for the post of Company Secretary. He was unsuccessful, which caused some general upset. At the club AGM a shareholder was reported in the local press as saying “ a more gentlemanly player never kicked a ball. He suggested that the board should come to terms with Boyle. (Loud applause).” The club who had previously given him a benefit match, let him go on a free transfer.
Dundee F.C. were quick to obtain his signature in June 1902. The Evening Telegraph reported that he “Stands 5’6”. An alert, untiring half back, who is just as much at home in the centre as on the wing. Although about 30 years of age, and on the old side, Boyle should prove a capital player for Dundee.”
He made his debut at home against Queen’s Park, winning 2-0. The 1902-03 season saw him make 16 appearance in the League, and five in the Scottish Cup. He became a mainstay of the team for the next two seasons. By 1906 his playing career was nearing its end. His final match in dark blue was in an away match versus Hearts. Although now in his late thirties he was still as dogged and determined as ever, the Evening Telegraph reporting “Boyle had a tussle with Dickson, in which the Edinburgh man came off second best, the spectators howled for Dick’s dismissal, and whenever he went near the ball the howling was renewed.” It was also mentioned that he would make an “efficient manager”.
He decided to return to his previous career as a draughtsman, taking up a position as Caledon Shipyard. Registering himself as an amateur, he kept himself fit playing himself for the shipyard team. Dickie also became involved with the Dundee City Boys league, and refereed matches
He explained the longevity of his career as being down to lifestyle choices, he didn’t smoke or drink, “I don’t object to others doing so, but the footballer who wishes to excel can be doing with as little alcohol and nicotine as possible. I know players who smoke a good deal before a match; it does not seem to affect them, but the young player should learn to do without his pipe and cigarette on Saturday forenoon. He will feel all the fresher at the end of the ninety minutes.’
Dickie gained one cap for Scotland, when he was selected for a Scottish League representative side to play an English League XI in March 1892.
1910 saw him move back to the west coast, where he settled in Renton, whilst being employed in a Glasgow shipyard.
He died on the 24th May 1947 at the age of 77.