As the entire Balkan Peninsula becomes an integral part of the emerging Ottoman Empire (a process that concludes with the fall of Constantinople to Sultan Mehmed II in 1453), Wallachia becomse engaged in frequent confrontations and, in the final years of Mircea the Elder's reign, becomes an Ottoman tributary state.

Mircea (reigned 1386–1418), initially defeated the Ottomans in several battles (including that of Rovine in 1394), driving them away from Dobruja and briefly extending his rule to the Danube Delta, Dobruja and Silistra (ca.1400–1404).

He swings between alliances with Sigismund of Hungary and Jagiellon Poland (taking part in the Battle of Nicopolis), and accepted a peace treaty with the Ottomans in 1417, after Mehmed I takes control of Turnu Măgurele and Giurgiu.