Donaldson signed with Scottish Football League Second Division Airdrieonians from Cliftonhill Rovers in December 1888.
[2] The ensuing dispute between the two clubs was settled when he declared that as Blackburn had failed to register their form within the specified time he was therefore a Newton Heath player.
[4] In November 1897 he was suspended by Newton Heath for a breaching training regulations and placed on the transfer list[5] and a month later for an £80 fee joined Football League Second Division club Luton Town.
The transfers were the subject of a dispute between the clubs: a Football League tribunal set the fee at the £200 offered by Glossop rather than the £500 requested by Luton.
[8] In January 1900 owing to cost-cutting measures he was released by Ashford[9] and in February was subject of negotiations between Glossop – who had continued to hold his Football League registration – and Newton Heath who were looking to appoint him as there reserve team coach.