Vasily Yakovlevich Shchelkalov (Василий Яковлевич Щелкалов in Russian) (before 1566 – 1610 or 1611) and Andrey Yakovlevich Shchelkalov (Андрей Яковлевич Щелкалов) (before 1550 – c. 1597) were two diplomats and heads of the Posolsky Prikaz during the reigns of Ivan the Terrible, Feodor I, and Boris Godunov in Russia.
The name of Andrey Yakovlevich Shchelkalov first appeared in 1550, when he was entered in the so-called Book of a Thousand (Тысячная книга, or Tysyachnaya kniga).
Andrey Shchelkalov rose to power during the Oprichnina period of mass executions of well-known government officials possibly as early as 1570 (although some sources say 1573).
In 1581, Andrey Shchelkalov conducted negotiations with a papal legate Antonio Possevino, and with the English ambassador Jerome Bowes in 1583, which would write in a personal letter from August 12, 1584, that Andrey Shchelkalov and Nikita Romanov (a boyar, who started the Romanov bloodline) "considered themselves the tsars".
Andrey Shchelkalov left diplomatic service in 1594, took monastic vows and assumed the name of Theodosius.