Many studies have been carried out throughout the world on how street-connected children relate to the streets, but not enough of these studies are seen through a gender perspective. Hence, the general conception of street-connected children is in some manner still mainstreamed, which casts an image claiming all children in the same category. This demonstrates that there is currently a missing gap of knowledge. This study covers whether the role of gender could affect the lives of the children that live and work on the streets, through a qualitative research in the field with 28 interviewees. These interviews were largely conducted in Brikama, Serekunda, Topkunda, Farafenni, Madina Salaam and Bakau in The Gambia, where the majority of the Gambian NGOs and street-connected children is located. The results from analysing these interviews pointed towards the same pattern: that there were a few similarities in the livelihoods of the street-connected boys and girls. However, the differences concerning their livelihoods on the streets were greater since the findings demonstrated that their challenges and opportunities of achieving the Ten Central Human Capabilities were different. Street-connected boys and street-connected girls were both exposed to child labour. The main difference was, street-connected boys, who lived in groups, worked in car garages, fish industries and for shop owners, while the few girls who permanently lived on the streets, were alone and sexual exploited. This research is thus not merely a contribution to the studies of street-connected children, but how gender is relating to the streets. Furthermore, a contribution to improve these vulnerable children’s livelihoods and also increase the awareness through the perspective of humanities, which might be crucial in future policy recommendations and research.