We report on what is to the best of our knowledge the longest 50-Gb/s/λ O-band wavelength-division multiplexed (WDM) transmission. A pair of in-house built bismuth-doped fiber amplifiers (BDFAs) and the use of Kramers-Kronig detection-assisted single-sideband transmission are adopted to overcome the fiber loss and chromatic dispersion, respectively, in a reach-extended O-band coarse WDM (CWDM) system with a channel spacing of ∼10 nm. Through experiments on an amplified 4×50-Gb/s/λ direct-detection system based on booster and pre-amp BDFAs, we show the superior performance of single-sideband transmission in terms of both optical signal-to-noise ratio sensitivity and uniformity in performance amongst CWDM channels relative to double-sideband transmission after both 75-km and 100-km lengths of single-mode fiber. As a result, up to 100-km reach with comparable performance at all 50-Gb/s channels was achieved without the need for in-line optical amplification.