Purpose Vitreomacular traction (VMT) is a condition characterized by an incomplete posterior vitreous detachment resulting in traction on the macula and possible subsequent decrease in visual acuity and/or other symptomatology. Vitreomacular traction often presents as a unilateral condition, with some cases developing bilaterality with disease progression. The natural course and presentation of VMT vary widely among individuals. There is no extensive literature regarding the prevalence of VMT in the general population; therefore, little is known on the laterality. Case Reports We present eight cases of bilateral VMT encountered in a primary care setting. These cases highlight the variability in presentation, symptomatology, and clinical outcome between and within eyes of patients with bilateral VMT. Conclusions Spectral-domain optical coherence tomography has provided new insight into VMT by allowing better visualization of the vitreoretinal interface. Using spectral-domain optical coherence tomography, eight unique cases of bilateral VMT were confirmed and classified. However, despite the bilaterality noted in each case, the clinical presentation and course of disease varied among patients. Because of the paucity of epidemiological data regarding VMT, the laterality of the condition, risk factors for involvement, and overall prognosis remain unclear.