The present paper describes the results of an analysis of individual differences-using multi-dimensional strategies-in stressful life event data collected from a representative sample of homeless people (N = 289) in Madrid, Spain, which revealed the existence of three subgroups within the sample. Each subgroup can be defined by the following differentiating characteristics: The first cluster (n = 124) was characterized by economic problems; the second (n = 80) by health problems, alcohol abuse, and death of one or both parents; and the third cluster (n = 50) by an accumulation of stressful life in childhood events and alcohol abuse. In order to define the subgroups, the article also examines the differences found in other variables such as total duration of homelessness, mental and physical health status, and social support availability, among others. The existence of such subgroups within the homeless population emphasizes the importance of designing different interventions for each of these groups, adapted to their diverse needs.