In this work, tribological characteristics of thin films composed of entangled carbon nanotubes (CNTs) were investigated. The surface roughness of CNT thin films fabricated via a dip-coating process was controlled by squeezing during the process with an applied normal force ranging from 0 to 5 kgf. Raman spectra and scanning electron microscopy (SEM) images of the thin films were obtained to estimate the influence of the squeezing process on the crystallinity of the CNTs. The analysis revealed that squeezing could reduce surface roughness, while preserving the crystallinity of the CNTs. Moreover, the surface energy of the cover glass used to press the CNT thin film was found to be the critical factor controlling surface roughness. A micro-tribometer and macro-tribometer were used to assess the tribological characteristics of the CNT thin film. The results of the tribotest exhibited a correlation between the friction coefficient and surface roughness. Dramatic changes in friction coefficient could be observed in the micro-tribotest, while changes in friction coefficient in the macro-tribotest were not significant.