The recent emergence of efficient O-band amplification technologies has enabled the consideration of O-band transmission beyond short reach. Despite the O-band being a low chromatic dispersion (CD) window, the impact of CD will become increasingly significant when extending the reach of direct-detection (DD) systems. In this work, we first numerically investigate the 3-dB bandwidth of single-mode fibers (SMF) and the CD-restricted transmission reach in intensity-modulation DD systems, confirming the significant difference between low- and high-dispersion O-band wavelengths. We then carry out experimental transmission studies over SMF for distances of up to 70 km at two different wavelengths, the low-dispersion 1320 nm and the more dispersive 1360 nm, enabled by the use of an O-band bismuth-doped fiber amplifier as a preamplifier at the receiver. We compare three 50-Gb/s optical DD formats, namely, Nyquist on-off keying (OOK), Nyquist 4-ary pulse amplitude modulation (PAM4) and Kramers-Kronig detection-assisted single-sideband quadrature phase shift keying (KK-QPSK) half-cycle subcarrier modulation. Our results show that at both wavelengths, OOK and QPSK exhibit better bit error rate performance than PAM4. When transmitting over 70-km of SMF at the less dispersive wavelength of 1320 nm, 50-Gb/s OOK modulation offers more than 1.5-dB optical power sensitivity improvement at the photodiode (PD) compared to 50-Gb/s QPSK. Conversely, at 1360 nm, the required optical power to the PD can be reduced by more than 3 dB by using QPSK instead of OOK.