We present the results from an optical spectroscopic analysis of the massive stars HD 37366 and HD 54662 . We find that HD 37366 is a double-lined spectroscopic binary with a period of 31.8187 \pm 0.0004 days , and HD 54662 is also a double lined binary with a much longer period of 557.8 \pm 0.3 days . The primary of HD 37366 is classified as O9.5 V , and it contributes approximately two-thirds of the optical flux . The less luminous secondary is a broad-lined , early B-type main-sequence star . Tomographic reconstruction of the individual spectra of HD 37366 reveals absorption lines present in each component , enabling us to constrain the nature of the secondary and physical characteristics of both stars . Tomographic reconstruction was not possible for HD 54662 ; however , we do present mean spectra from our observations that show that the secondary component is approximately half as bright as the primary . The observed spectral energy distributions ( SEDs ) were fit with model SEDs and galactic reddening curves to determine the angular sizes of the stars . By assuming radii appropriate for their classifications , we determine distance ranges of 1.4 – 1.9 and 1.2 – 1.5 kpc for HD 37366 and HD 54662 , respectively .