This prospective, double-masked, contralateral study aimed to analyze and compare daytime changes in pre-lens tear film (PLTF) stability and optical quality in symptomatic subjects wearing two contact lenses (CL). A secondary goal was to assess the performance of the PLTF by using dynamic topography techniques and analyzing surface asymmetry and irregularity indexes (SAI and SRI, respectively). Measurements were conducted on 20 symptomatic subjects (OSDI score > 13). Participants were fitted contralaterally and randomly with spherical Delefilcon A and Stenfilcon A CLs and underwent a series of measurements over 3 consecutive days: three in the morning (after 1-2 h of CL wear) and three in the afternoon (after 7-9 h of CL wear). High- and low-contrast visual acuity (HCVA and LCVA, respectively), pre-lens NIBUT, and dynamic topography were assessed. The contralateral fit of the two lenses allowed a direct and better comparison between them since they were exposed to the same conditions during the day. Consequently, both lenses demonstrated similar performance in HCVA, LCVA, and PLTF stability, with no statistically significant differences between them, although some fluctuations were observed throughout the day. Dynamic topography proved sensitive in evaluating temporal changes in the PLTF. The SRI index showed greater sensitivity to topographic changes due to lacrimal destabilization, making it potentially valuable for evaluating dry eye patients.