This study analyses the connection between extreme rainfall events in Jeddah, Saudi Arabia, and synoptic-scale weather patterns over the Arabian Peninsula. Mean rainfall follows a decreasing trend; however, the number of rainy days has increased. Interestingly, extreme rainfall is becoming less frequent but shows an increased intensity. Here we utilize self-organizing maps (SOMs) to identify the weather patterns of the most intense rainy days and the synoptic systems causing extreme rainfall in the Jeddah region. Three main weather patterns that cause heavy rainfall events over Jeddah during the cooler months (November–April) are identified, all reflect tropical-extratropical interactions. Extreme events in the early period (1979–1998) are characterized by a stronger tropical influence and local precipitation patterns, while a stronger extratropical forcing and higher extreme rainfall amounts are spotted in the late period (1999–2018). Our results suggest that in recent decades, the mechanism causing extreme rainfall over the city of Jeddah has shifted toward a weather regime with stronger extratropical influence.