Cambodia has established diplomatic relations with North Korea since mid-1960s. These relations were fostered by Prince Norodom Sihanouk and the late Great Leader Generalissimo Kim Il Sung. These relations were strengthened over the years through high-level visits by the leaders of the two countries. For past decades, the relations between the two countries had been categorized as the unique ones based on strong personal tie of the two leaders rather than the national interests, and they were not based on geopolitical location and cultural connection. However, death of Kim Il Sung, then Kim Jung Il, and finally King Norodom Sihanouk, marked the end of the special relationship between Cambodia and North Korea – and with no Princes or Great Leaders linking arms, the two nations’ destinies hardly seem linked either. Eventually, the relations between the two countries have become nominal ones. This paper seeks to examine the historical review of the bilateral relations, present landscape of relations with focusing on the past legacy, and the roles played by Cambodia between the North and the South Korea.