Rainfall irregularity in Mediterranean regions is a characterizing feature of their climate. The aim of this manuscript is to analyze, in a climate change context, the evolution of this irregularity in Barcelona. A very long monthly database (1786–2023) enables detailed analysis of rainfall evolution, with its irregularity quantified using the concept of disparity, the trends of which are assessed using moving windows and a modified Mann–Kendall test. The relationship between disparity and the Western Mediterranean Oscillation index (WeMOi) is also explored. Additionally, the study compares rainfall amounts to the 1961–1990 reference period and evaluates autumn’s contribution to annual totals. A significant and increasing disparity trend over the years is detected for the autumn months. While correlations between disparity and WeMOi are limited, the WeMOi and monthly precipitation are significantly correlated for two autumn months, October and November, and for December, aligning with previous studies. This suggests the potential influence of the WeMOi fluctuations on future rainfall during these three months. Recent evidence of the increasing autumn irregularity is seen in the consecutive low-rainfall years of 2021, 2022 and 2023, which stand out as the driest since 1835, with the last two autumns ranking among the 5% driest.