Simple Summary: This retrospective study aims to classify a series of pituitary neuroendocrine tumours (PitNETs), typified according to the WHO 2017 recommendations, using Trouillas et al.’s clinicopathological classification from 2013. We analysed 166 patients who underwent PitNET surgery from 2013 to 2023. The tumours were identified according to the gene and immunohistochemistry expression of pituitary transcription factors and adenohypophyseal hormones. The PitNETs were graded based on the invasion observed in MRI and the Ki-67 index. The study found that grade 2a and 2b tumours, T2 signal intensity ratio (SIR), and silent corticotroph tumours were associated with lower progression-free survival rates. Tumour volume and T2 SIR were inde...