Background/Objective: The aim of this retrospective study was to compare corneal parameters and compliance using a Pentacam HR–Scheimpflug (Pentacam HR) and a swept-source OCT Casia (Casia) in keratoconus (KC) patients post penetrating keratoplasty (PKP) and KC patients without PKP, as well as a control group. Pachymetry measurements were also analyzed using a spectral domain OCT Solix (OCT Solix), Pentacam HR, and Casia. Methods: The study included 71 patients (136 keratoconic eyes; group A), 86 eyes with KC post-PKP (group B), 50 eyes with KC without PKP (group C), and 52 control participants (104 eyes). All participants were adults, Polish Caucasian, and met specific inclusion criteria. Patients with ophthalmological or systemic diseases, cognitive impairment, or pregnancy were excluded. Corneal parameters were measured using two devices (Casia and Pentacam HR), while pachymetry was assessed with three devices (Casia, Pentacam HR, and OCT Solix), with the inter-device agreement and group differences analyzed. Results: Significant differences (p < 0.05) were found across all groups. The post-PKP KC eyes showed significant differences in all front parameters and K2 and Astig. back, while the non-PKP KC eyes showed differences in the K1 back (p = 0.025). The controls displayed differences in all parameters except front astigmatism (p = 0.61). The Pentacam HR overestimated the thinnest corneal thickness (TCT) compared to the OCT Casia across groups. The inter-device agreement was excellent for the anterior parameters (ICC > 0.9) but good for the posterior parameters and TCT. Conclusions: This study highlights significant variability in corneal and pachymetry measurements across devices, with OCT Casia providing more consistent and clinically reliable results than Pentacam HR. Clinicians should exercise caution when using these devices interchangeably, particularly for posterior parameters and TCT.