Objective: This study was conducted to compare the correlation between Pap smear and colposcopic biopsy findings in premenopausal and postmenopausal women. Study design: A total of 68,738 ThinPrep Pap smears were done in 2011 in our institution, and of these, 865 of the women (787 premenopausal and 78 postmenopausal) had subsequent colposcopic directed biopsies performed within 3 months of obtaining the results. Results: We discovered that 52.5% of the Pap smears in postmenopausal women versus 33.6% in premenopausal women were classified as false positive (FP), with respect to the biopsy, and of these, 47.6 vs. 17% cases had no transformation zone (TZ) on the subsequent biopsies, respectively. Interestingly, with respect to high-risk human papilloma virus (hrHPV) testing in patients having both Pap smear and biopsies performed, we found the Pap smear diagnoses were a better predictor of positive hrHPV than the respective colposcopic biopsies. Conclusion: As many of the FP postmenopausal women had an absent TZ (47.6%) on biopsy, and because the majority (83.3%) of those which had hrHPV testing were positive, we suggest that this indicates a potential sampling error on biopsy, perhaps due to an inability to visualize the involved area in older women due to an upward migration of the TZ.