Introduction: This is the first published study on decompression illness (DCI) and its treatment in Finland. Diving conditions are demanding, as even in the summer the water temperature below 20 meters’ sea/fresh water (msw/mfw) is 4–10°C. Technical diving has become more popular over the years, so the emphasis of this study was to describe DCI in technical divers and compare it with non-technical recreational divers. Methods: This study includes by estimation over 95% of all hyperbaric oxygen-treated DCI patients during the years 1999–2018 (n = 571). The cases were divided into technical divers (n = 200) and non-technical divers (n = 371). We focused on the differences between these two groups. Technical diving was defined as the usage of mixed breathing gases, closed circuit rebreather diving or planned decompression diving. Results: The mean annual number of treated DCI cases in Finland was 29 (range 16–38). The number of divers treated possibly indicate a shift towards technical diving. Technical dives were deeper and longer and were mainly performed in cold water or an overhead environment. Technical divers were more likely to utilize first aid 100% oxygen (FAO2) and sought medical attention earlier than non-technical divers. Symptom profiles were similar in both groups. Recompression was performed using USN Treatment Table Six in the majority of the cases and resulted in good final outcome. Eighty two percent were asymptomatic on completion of all recompression treatment(s). Conclusion: This 20-year observational study indicates a shift towards technical diving, and hence a more demanding and challenging style of diving among Finnish divers, with a surprisingly constant number of DCI cases over the years. There is still need for improvement in divers’ education in use of FAO2 for DCI symptoms. Fortunately, the outcome after recompression therapy is generally successful.