Ivan Shishman ya mutu a shekara ta 1395 lokacin da Ottomans , karkashin jagorancin Bayezid I, suka dauki sansaninsa na karshe na Nikopol.A shekara ta 1396, Ivan Sratsimir ya shiga yakin Crusade na Sarkin Hungarian Sigismund, amma bayan da sojojin Kirista suka ci nasara a yakin Nicopolis, nan da nan Ottomans suka hau kan Vidin suka kwace shi, wanda ya kawo karshen mulkin Bulgarian na da.Yakin Nicopolis ya faru ne a ranar 25 ga Satumba 1396 kuma ya haifar da fatattakar sojojin 'yan ta'adda na Hungarian, Croatian, Bulgarian, Wallachian, Faransanci , Burgundian, Jamusanci, da dakaru daban-daban (da taimakon sojojin ruwa na Venetian ) a hannun wani sojan ruwa. Daular Ottoman, ta tayar da kewayen sansanin Danubian na Nicopolis kuma ya kai ga ƙarshen daular Bulgaria ta biyu.Yawancin lokaci ana kiransa da Crusade na Nicopolis kamar yadda ya kasance ɗayan manyan Crusades na ƙarshe na Tsakiyar Tsakiya, tare da Crusade na Varna a 1443-1444.