For a small minority of people, gambling can cause poor financial and/or health outcomes. The manner in which problem gamblers experience their lives and themselves in relation to others may play a crucial role in the development and/or maintenance of their gambling. The aim of this study was to examine whether there are any differences between online problem gamblers and offline problem gamblers in their experience of the consequences of their gambling behaviour in relation to quality of life and wellbeing. The analysis of interview data from six online problem gamblers and nine offline problem gamblers revealed that the use of gambling to manage negative emotional states was evident across all participants irrespective of gambling medium, and that problem gamblers experience a high preoccupation with gambling leading to personal, social, and financial negative consequences. The study revealed very few differences between the two groups of problem gamblers. The health problems experienced by the problem gamblers included mental health problems, physical health problems, and emotional health problems. The study has clear implications for clinicians working with problem gamblers, as excessive gambling causes serious problems and in some cases, the gambling behaviour may be seen as a symptom of experiential dysfunction that must be addressed along with the problematic behaviour.