Battle of Ihtiman

Michael Asen IV belonged to the Bulgarian royal line of the Asen dynasty and was Ivan Alexander's eldest son. He is believed to have been his father's co-ruler during his lifetime. When the Ottomans invaded the country in 1354, they advanced towards Plovdiv and Sredets. They were met by Michael IV Asen and his troops. 

The Bulgarian troops suffered defeat in the battle, and Michael was killed.