He was one of the three sons of Ahmed Khan bin Küchük, the man who lost Russia in 1480.
In 1501, Khan Sheikh Ahmed attacked Muscovite forces near Rylsk, Novhorod-Siverskyi, and Starodub.
[3] According to the accounts of the Bychowiec Chronicle Sheikh Ahmed gave the rule of these occupied cities to the Lithuanian diplomat of Ruthenian origin Michał Chalecki.
Lithuanian Grand Duke Alexander Jagiellon was preoccupied with his succession in the Kingdom of Poland and did not participate in the campaign, failing to provide necessary support.
A harsh winter combined with burning of the steppe by Meñli I Giray, Khan of the Crimean Khanate, resulted in famine among Sheikh Ahmed's forces.