Francis Henry Medcalf (May 10, 1803 – March 26, 1880) was a Canadian millwright, iron founder, and Mayor of Toronto during the periods 1864–1866 and 1874–1875.

[1] He married Mary Harrison in Philadelphia before returning with her to Canada in 1839 to run several foundries in Toronto;[2] they had four sons and two daughters together.

He opened the Don Foundry and Machine Shop in 1847, which specialized in the production of agricultural machinery and steam engines.

Between 1867 and 1873, the mayor was selected by Toronto City Council rather than by popular vote, but when the electoral system was restored in 1874 he was re-elected for another two terms until he was defeated by the Conservative member Angus Morrison in 1876.

[1] Medcalf's nickname in politics was "Old Squaretoes",[3] a reference to his foundry work boots, an image he used to promote his "rags-to-riches story".