This article aims to outline the history of Turkey’s relations with Russia in the energy sector. The energy relationship between these two competing states dates back to the early 19th century when the Ottoman Empire fulfilled its coal and oil demands with Russian supplies. The history of Ottoman-Russia and later Turkey-Russia energy relations is an important aspect of the aforementioned states’ histories that needs to be unearthed and examined to better understand the complex relationship these states currently share. For instance, the complications that surround the recent natural gas pipeline projects such as Nabucco, South Stream, and Blue Stream II, reminiscent of previous projects in the region, can be better understood if one analyzes the semi-successful Baghdad railway project of the early 20th century. This article aims to analyze and highlight the complex relationship of yesterday in Turkey-Russia energy relations in an effort to shed light on the complexities of that same relationship today. The story will sound amazingly similar albeit with different actors.