Shchenya took an active part in the Muscovite–Lithuanian Wars against the Grand Duchy of Lithuania and border disputes and skirmishes, which had preceded the war. In 1493, Shchenya and his relative Prince Vasili Ivanovich Patrikeyev (also known as Vassian Kosoy) captured the city of Vyazma and transferred its princes to Moscow. During the Russo-Swedish War (1496–1499) his army devastated Finland. In 1499, under the leadership of Prince Daniil Kholmsky, Shchenya defeated the Grand Hetman of Lithuania Konstanty Ostrogski in the Battle of Vedrosha and took him prisoner.