Obstructive sleep apnea (OSA) is a sleep-related breathing disorder (SRBD) hallmarked by upper airway collapsibility and obstruction leading to nocturnal hypoxia and sleep arousals. Diabetes mellitus (DM) is a chronic medical malady which stems from an aberration in the glucose metabolism leading to multisystemic complications and eventually ends organ damage. Both these disorders are independently major public health concerns by virtue of their momentous morbidity, mortality and healthcare albatross. The liaison between these two leviathans is enigmatic and multifarious. Prima facie they share a common predisposing factor of obesity. OSA is associated with impairment of glucose metabolism and predisposes the individual to the development of DM. Moreover DM serves as a risk factor for OSA in conjunction with the other components of the metabolic syndrome. Untreated DM leads to aggravation of the severity of OSA while untreated OSA leads to suboptimal glycemic control and propagates complications of DM. This intricate relationship between DM and OSA is a fertile and deficiently fathomed terrain for contemplative research. We hereby make a humble endeavor to decipher and simplify the Daedalean association.