Heavy rainfall due to tropical cyclones (TCs) in the North Indian Ocean (NIO) adversely impacts nations frequently. Though extensive research has focused on TCs in the NIO, less attention has been given to the connection between TCs and extreme events in Sri Lanka. This study examined atmospheric characteristics during sixteen extreme events, focusing on linkages between TCs, the Indian Ocean Dipole (IOD), and mechanisms behind heavy rainfall associated with TCs over Sri Lanka. The results showed that in the pre-monsoon period, TCs move northward with high water vapor (WV) content accumulated in the Southern Hemisphere. This main WV flow over the equatorial Indian Ocean (EIO) is connected with TCs, causing considerable damage in the southwestern part of Sri Lanka. During negative IOD years, strong westerly winds create cyclonic circulations on either side of the equator. Conversely, during the post-monsoon period, the IOD phase has no significant effect. TCs generally followed westward tracks, supported by winds from the Northern Hemisphere, and caused heavy rainfall in the Eastern, Northern, and Northcentral provinces in Sri Lanka. These TCs are isolated from the main WV flow over EIO. Such observed common characteristics during pre-monsoon and post-monsoon seasons are key factors contributing to extreme rainfall in Sri Lanka.