After the assassination of Ahmed Khan in 1481, his sons feuded for power and it only further weakened the Horde. The Horde, historically allied with the Grand Duchy of Lithuania, was fighting with the Crimean Khanate, allied with the Grand Duchy of Moscow.
In 1500, the Muscovite–Lithuanian War resumed. Lithuania once again allied with the Great Horde. In 1501, Khan Sheikh Ahmed attacked Muscovite forces near Rylsk, Novhorod-Siverskyi, and Starodub. Lithuanian Grand Duke Alexander Jagiellon was preoccupied with his succession in the Kingdom of Poland and did not participate in the campaign. 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. Many of his men deserted him and the remainder was defeated on the Sula River in June 1502.
Sheikh Ahmed was forced into exile. He sought refuge at the Ottoman Empire or an alliance with the Grand Duchy of Moscow, before turning to the Grand Duchy of Lithuania. Instead of helping its former ally, the Grand Duchy imprisoned Sheikh Ahmed for over 20 years. He was used as a bargaining chip in negotiations with the Crimean Khanate: if the Khanate did not behave, Sheikh Ahmed would be released and would resume his war with the Khanate. Meñli I Giray became a reluctant ally of Lithuania. Sheikh Ahmed was held in Trakai and moved to Kaunas Castle after an escape attempt.
- Howorth (1880), p. 327
- Kolodziejczyk (2011), p. 26
- Howorth (1880), p. 346
- Kolodziejczyk (2011), p. 27
- Howorth (1880), p. 463
- Kolodziejczyk (2011), p. 36
- Howorth (1880), p. 347
- Kolodziejczyk (2011), p. 66
- Kolodziejczyk (2011), p. 68
- Howorth, Henry Hoyle (1880). History of the Mongols from the 9th to the 19th Century. 2. Longmans, Green, and Co. OCLC 49793717.
- Kolodziejczyk, Dariusz (2011). The Crimean Khanate and Poland-Lithuania: International Diplomacy on the European Periphery (15th-18th Century). A Study of Peace Treaties Followed by Annotated Documents. The Ottoman Empire and its Heritage. BRILL. ISBN 9789004191907.