Teams Herbert Caldwell played for

MiscellaneousGentlemen of Loretto School (1879)
 Loretto School (1880)
 South of Scotland (1882)
 Edinburgh (1883-1889)
 Fettesian Lorettonians (1884-1892)
 Scotland (1886)
 Grange (1886-1887)
 Bryn-y-Neuadd (1887)
 Marylebone Cricket Club (1888-1889)
 Gentlemen of Edinburgh (1889)
 East of Scotland (1890)
 Lasswade (1893)