This 1921 FA Cup Winners Medal was awarded to Spurs player Bob McDonald, who joined the club from Inverness Caledonian in 1919. Playing full back, he made a total of 125 appearances in all competitions during his career at White Hart lane, the highlight being involved in the 1921 FA Cup winning side.
In 1927 he transferred to Clapton Orient, and went on to play a further 37 matches.
The 1921 final saw Tottenham take on Wolves at Stamford Bridge, with Spurs winning by a single goal, scored by Jimmy Dimmock eight minutes into the second half. The team was presented with the FA Cup by King George V.