Geographically, Bangladesh is considered to be one of the most cyclone-prone areas in the world. The super cyclone Sidr in 2007 was one of the most devastating disasters to have ever occurred in Bangladesh, having wind speeds of 223 km/h with a tidal surge of 6.1–7.6 m high. In order to draw a pre- and post-Sidr damage and management scenario, a survey was conducted at Dumki upazila, Patuakhali district in Bangladesh with a pretested questionnaire. Primary data were collected through a questionnaire, while secondary data were collected from pertinent offices as well as academic journals. The major focus of this study was to assess the state of pre-Sidr tree plantations (woody and fruit trees), the devastation caused by Sidr on these tree plantations, and post-Sidr recovery and further sustainable management initiatives to counteract a possible future neo-Sidr. The post-Sidr study showed that about 16.84 million woody and fruit trees were uprooted by Sidr. A total of 3,120 rain tree (Samanea saman L.), 7,548 mahogany (Swietenia mahagoni L.), 1,444 royal siris (Albizzia richardiana L.), 702 white siris (Albizzia procera L.), 1,214 mango (Mangifera indica L.), 1,092 coconut (Cocos nucifera L.), 1,380 jackfruit (Artocarpus heterophyllus L.), and 7,640 betel nut (Areca catechu L.) trees were sampled among which 922, 1,662, 382, 210, 106, 38, 362, and 1,652 trees, respectively, were markedly damaged by Sidr. Sexually propagated woody trees with a damaged taproot were vulnerable to heavy wind during the cyclone. Fruit trees were more resistant to the cyclone than other types of trees, and the lack of proper tree training and pruning was one of the principal causes of the severe damage to woody trees. Hence, plantations of woody tree saplings with damaged taproots are strongly discouraged. However, proper training and pruning of homestead trees together with plantation of fruit trees rather than woody trees is suggested as a possible effective management strategy to protect the homestead ecosystem from devastation by future cyclones in Bangladesh.