Occasionally, Hashimoto's thyroiditis (HT) and papillary thyroid carcinoma (PTC) share similar nuclear features. The current study aims to quantify the differences between the investigated specimens of HT-associated PTC versus the HT alone, to reduce the subjective experience of an observer, by the use of fractal parameters as well as gray-level co-occurrence matrix (GLCM) textural parameters. We have analyzed 250 segmented nuclei per group (nn = 25 per patient and np = 10 patients per group) using the ImageJ software (NIH, Bethesda, MD, USA) as well as an in-house written code for the GLCM analysis. The mean values of parameters were calculated for each patient. The results demonstrated that the malignant cells from the HT-associated PTC specimens showed lower chromatin fractal dimension (p = 0.0321) and higher lacunarity (p = 0.0038) compared with the corresponding cells from the HT specimens. Also, there was a statistically significant difference between the investigated specimens, in the contrast, correlation, angular second moment, and homogeneity, of the GLCM corresponding to the visual texture of follicular cell chromatin. The differences in chromatin fractal and GLCM parameters could be integrated with other diagnostic methods for the improved evaluation of distinctive features of the HT-associated PTC versus the HT in cytology and surgical pathology specimens.