Prince Handayaningrat was the head of the Pengging land and was known as Ki Ageng Pengging Sepuh. After he died, Kebo Kenanga replaced him with the nickname Ki Ageng Pengging. It is said that Ki Ageng Pengging Sepuh died from keris warangan poison after being stabbed by the keris of Sunan Ngudung, the father of Sunan Kudus, during the war between Demak and Majapahit. Sunan Ngudung was then killed by Adipati Terung (Pecat Tanda Terung). The three main graves in the area of ??the Ki Ageng Pengging Sepuh Boyolali Tomb are located under the tall, shady Kepuh Tree. According to the caretaker, the very impressive tree is more than 600 years old. The two adjacent graves are the graves of his wife, Retno Pembayun. Meanwhile, the other grave is the Tomb of Kebo Amiluhur, the youngest of Ki Ageng Pengging Sepuh who had no children. Like his father, Kebo Kenanga also embraced Islam and became the best student of Syaikh Siti Jenar. However, Kebo Kanigara remained loyal to the old religion (Hinduism) and is said to have died while meditating at the peak of Mount Merapi. There is also a grave on the edge of the surrounding fence called the grave of Widuri, who is known as the only child of Kebo Kanigara. Widuri is the child of Kebo Kanigara, who married Arya Salaka or Ki Gede Banyubiru (Interview with Narto, June 23, 2019).

As a student of Syaikh Siti Jenar, Ki Ageng Pengging II (Kebo Kenanga) refused to submit to the authority of the Sultan of Demak. Finally, like his father, Kebo Kenanga was sentenced to death by the Sultan of Demak, as experienced by his teacher, Syaikh Siti Jenar. The Demak Kingdom ended when the political power after Sultan Trenggana weakened further, coupled with the deaths of Sunan Prawata and Arya Panangsang. Raden Mas Karebet or Jaka Tingkir, son of Kebo Kenanga, founded the Pajang Sultanate and continued Islamic politics in Java. However, the Pajang Sultanate also did not last long. After his death, the Pajang Sultanate was replaced by the Mataram Kingdom founded by Danang Sutawijaya and his father Ki Ageng Pemanahan. The land of Mataram, or Mentaok, was a gift land obtained by Ki Ageng Pemanahan after successfully killing Arya Panangsang. Danang Sutawijaya or Panembahan Senapati was the grandson of Ki Ageng Henis, son of Ki Ageng Selo who was buried in Grobogan.