The 1816 special elections for Maryland's 5th congressional district were to fill two separate vacancies. The 5th district was a plural district, with two seats. Both seats were vacated, the first by Representative Nicholas R. Moore (DR) in 1815, before the 14th Congress even met, and the second by Rep. William Pinkney (DR) on April 18, 1816, after being named Minister to Russia.
The first special election was held on January 27, 1816, to replace Moore.
Smith took his seat in the 14th Congress on February 4, 1816.
The second election was held on September 3 to fill the vacancy left by Pickney's resignation.
Little took his seat on December 2, 1816, at the start of the Second Session.