When the Asian conquerors reached the centre of the Balkans, the rulers of Serbia and Bosnia were frightened and concluded an alliance for joint action against Murad. The united Serbian and Bosnian troops dealt a crushing blow to the Turks in the big battle near the town of Plochnik in 1387. The Bulgarian Tsar joined the Serbo-Bosnian alliance which provoked an immediate wrathful reaction on the part of the Sultan. In 1388 a numerous Turkish army crossed the Balkan Range and conquered almost the whole of Northeastern Bulgaria without the city of Varna. Tsar Shishman was forced to reaffirm his vassal dependence from the Sultan and the terrible Ottoman hordes again set out for Serbia. In a battle which broke out at Kossovo Pole Murad I found his death but the Serbian troops, which had been joined by several Bulgarian feudal lords, were routed. Serbia also fell under vassal dependence from Turkey. .

The existence of the Bulgarian state became an obstacle on the way to the Ottomans' further penetration into Central Europe. In spite of its weakness and dependence, it presented a constant threat to the right flank of the Turkish troops which had penetrated deep into the west. That is why Murad's heir Bayazid I, The Light-ning, decided to put an end to the Turnovo Kingdom. In 1393 he invaded Moesia at the head of a numerous army and after a siege which Lasted three months, succeeded in capturing Turnovo.

One hundred and twenty boyars were massacred in the main church, thousands of Turnovo citizens were taken slaves and Patriarch Evtimi, who had headed the defence of Turnovo until the last moment, was sent into exile to the Rhodopes. Ivan Shishman hid himself in the Danubian stronghold of Nikopol, expecting help from the Hungarian King. The latter, however, never came to his assistance and Nikopol was captured and Ivan Shishman was killed. Only the Vidin Kingdom remained, but a Turkish garrison was also stationed in Vidin.

The Ottomans reached the frontiers of the then powerful Hungarian Kingdom, which forced the Hungarian King Sigismund to prepare in 1396 a big crusade against the Turks. The Ruler of Vidin Ivan Stratsimir opened the gates of his town to the crusaders and joined them with his troops, but the army of the crusaders suffered utter defeat. That was the end also of the Vidin Kingdom.

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