[2] Many members of his family took part in various revolutions of the 19th century as Greek War of Independence, Cretan revolt of 1866 etc.

The same period, according to Greek sources, his band made a successful ambush against komitadjis and after that Koukoulakis and his men avoid an operation that was held by the Ottoman Gendarmerie.

[6] In March 1905, Koukoulakis took part in the attack against the Bulgarian village of Zagoritsani ( today, Vasiliada).

During the attack, he entered the village from the north side along with his fellow Cretan leader, Ioannis Poulakas.

Koukoulakis died in 14 September 1909 in Athens due to health problems that he suffered from his time in Macedonia.