We report new results of a campaign to find Wolf-Rayet and O (WR/O) stars and high-mass X-ray binaries (HMXBs) in the Galactic center. We searched for candidates by cross-correlating the Two-Micron All-Sky Survey with a deep Chandra X-ray Observatory catalog of point sources in the Radio Arches region. Following up with K-band spectroscopy, we found two massive stellar counterparts to CXOGC J174555.3-285126 and CXOGC J174617.0-285131, which we classify as a broad-lined WR star of sub-type WN6b and an O Ia supergiant, respectively. Their X-ray properties are most consistent with those of known colliding-wind binaries in the Galaxy and the Large Magellanic Cloud, although a scenario involving low-rate accretion onto a compact object is also possible. The O Ia star lies 4.4 pc in projection from the Quintuplet cluster, and has a radial velocity consistent with that of the Quintuplet, suggesting that this star might have escaped from the cluster. We also present the discovery of a B2 Ia supergiant, which we identified as a candidate massive star using 8 micron Spitzer maps of the Galactic center in a region near the known massive X-ray-emitting star CXOGC J174516.1-290315. We discuss the origin of these stars in the context of evolving stellar clusters in the Galactic center.