In this work, we present spectroscopic investigations of hydrogen bonded complexes of CHF3 and CHCl3 with p-cresol and p-cyanophenol. The systems were chosen as the potential candidates bound by C−H···Y type hydrogen bonds that are known to exhibit unconventional blue shifts in the C−H stretching frequency. The two phenol derivatives chosen offer multiple hydrogen bonding acceptor sites. They also differ from each other in regard to the electron-donating/withdrawing ability of the para substituents which could dictate the global minimum structure in each case. The complexes were formed using the supersonic jet expansion method and were investigated using a variant of the IR-UV double resonance technique, namely fluorescence depletion IR (FDIR) spectroscopy. It was found that in the case of p-cresol the complexes were C−H···π bound in which the C−H stretch was blue-shifted. In the case of p-cyanophenol the complexes were C−H···N bound. In its fluoroform complex the C−H frequency was blue-shifted by 27 cm−1, whereas the chloroform complex gave an example of zero-shifted hydrogen bond. The ab initio computational studies indicated that for the CHCl3 complexes it is necessary to optimize the structures on the BSSE-corrected PES using the counterpoise method to correctly predict the magnitudes of the C−H frequency shift.