This longitudinal study focused on Namibian bilingual school children’s possible evidence of literacy development difficulties in two languages, namely, Herero, the children’s first language (L1) and English, their second language (L2), at Time 1 and Time 2 respectively. The study aimed to identify the cognitive and linguistic factors that may be related to literacy difficulties amongst this cohort of bilingual children. In addition, this study also assessed the assumptions of the central processing hypothesis and the script dependent/orthographic depth hypothesis with regard to literacy development and difficulties. Five cases of children who presented with evidence of poor literacy skills were selected from a sample of Grade 3 children for whom data were available at Time 1 (Grade 3) and Time 2 (Grade 4) of testing. At Time 1 there were 40 children and at Time 2, 30. The children who constituted the five cases were available at both Times 1 and 2. Generally, the results seemed to indicate that the five cases of children selected presented with literacy difficulties in both languages, indicating that if literacy difficulties occurred in the one language, they were also likely to occur in the other. This finding was consistent with the views of the central processing hypothesis.