The purpose of this study was to explore, describe and explain the transitions of individuals within a twinship from Grade R through to Grade 2, and thus offer an in-depth description of such participants’ transition experiences and perspectives. I focused my investigation on the overall transitions of the individuals within a twinship from Grade R through to Grade 2, and included variables such as stress, stressors, emotions, coping, and life skills. In this qualitative research study, I used a case study research design and conducted the research from both an interpretivist and social constructivist point of view. The primary participants in the research were two monozygotic individuals within a twinship (boys), their mother, and their Grade R, Grade 1 and Grade 2 teachers. I commenced the fieldwork when the individuals within a twinship were in Grade R and five years old, and tracked their transitions through until their Grade 2 year when they were eight years old. During their Grade R year, I taught the individuals within a twinship certain life skills by utilizing creative, age-appropriate worksheets and play activities. I continued to utilize such activities as a catalyst for collecting data throughout their Grade 1 and Grade 2 years. I also conducted semi-structured interviews with their mother and teachers. During visits to their school, I also observed the individuals within a twinship in their natural setting. The findings of the study suggest that the transition of the individuals within a twinship effected mainly trouble-free transitions from Grade R through to Grade 2 largely because of their positive attitudes and behaviour, their self-confidence, their pleasure in tackling new experiences, the security and support they enjoyed as co-individuals within a twinship, their satisfying friendships, the positive qualities of their teachers, the learned life skills, their realistic expectations of Grade 1 and Grade 2, and their ability to cope satisfactorily with their academic work. The negative stressors during these transitions were bullies and the disruption caused by disobedient children. A key finding of this study was that the transition of the individuals within a twinship to Grade 2 was, to some extent, more stressful than their transition to Grade 1 because of more demanding academic expectations in Grade 2. In spite of this, they characterized their Grade 2 holistically as enjoyable and rewarding. The learned life skills helped them to cope with various stressors, though the overall support structures of the individuals within a twinship were most influential in their largely trouble-free transitions from Grade R through to Grade 2. The learned life skills enabled the participants to deal successfully with bullies, to develop rewarding friendships, and with emotional control. It was apparent throughout this research that the individuals within a twinship enjoyed all the advantages of supportive social structures including a stable and safe home and school environment, This resulted in good relationships with each other, their parents siblings, teachers and friends.