Kilwinning, Ayrshire born goalkeeper Hugh MacDonald and played for a variety of local junior clubs including Ayr Academicals in 1896, Ayr Westerlea and Maybole in 1897, before joining St Bernard’s in 1898. A spell at Hearts of Beath later in 1898 was followed by a year with Ayr from 1899, but he returned to Hearts of Beath in 1900 before re-joining Ayr in 1902.
He joined Beith in 1903, before moving south to London to join First Division Woolwich Arsenal in January 1906. MacDonald was understudy to Arsenal’s regular goalkeeper, England international Jimmy Ashcroft, and played only two League games in what was to be his first spell at Arsenal, his Football League debut coming against Blackburn Rovers on 17th February 1906. At the end of the 1905-06 season he moved to Southern League Brighton & Hove Albion and spent two years there.
In May 1908 he returned to Woolwich Arsenal after they sold Ashcroft to make ends meet, and McDonald was an ever-present for the entire 1908-09 season, and only missed two games of 1909-10. He left Arsenal in July 1910 for Oldham Athletic, spending just over one season there making 44 appearances before moving to Bradford Park Avenue in December 1911, where he made 29 appearances over the next twelve months.
In December 1912 he returned to Arsenal for a third time, making him the only player to have played for the club in three separate spells. As of June 2010, the only other players to have rejoined the club are John Lukic, Jock Rutherford, Martin Keown, Sol Campbell and Jens Lehmann who all rejoined only once. He took over from Harold Crawford and played 18 of the last 21 League games of the 1912-13 season, but he couldn’t prevent Arsenal being relegated to the Second Division.
MacDonald left Arsenal for a third and final time in November 1913, having been ousted from the team by Joe Lievesley. In total he made 103 appearances for Arsenal across his three spells with the club. He saw out his career with first Fulham, joining them in November 1913 and making 8 appearances, and then with Southern League Bristol Rovers, joining them in 1914, before the First World War intervened and ended peacetime football in May 1915, and during the War MacDonald served in the British Army. He died in August 1920 aged 36 after suffering the effects of poison gas inhaled in the trenches during the War.