Educated at Winchester School, Thomas Gillespie soon showed his rowing talent and in his final year, was captain of the rowing club, as well as playing in the rugby XV. He went up to New College, Oxford, in 1911, and was a member of the college rowing eight for three successive years, and was twice part of the crew that was Head of the River.
At the outbreak of World War I, Gillespie obtained a commission into the King’s Own Scottish Borderers, and was sent on operations abroad almost immediately. It was whilst obeying orders to advance across the La Bassée Canal in France, that Gillespie was killed. His brother Alexander was also killed in action less that a year later The UK television presenter Tom Heap is the great nephew of Thomas Gillespie.