This study investigated the challenges of teaching mathematics in senior secondary schools in Kenema city, the Eastern region of Sierra Leone. The study made use of the survey design. The population comprised all Mathematics teachers and year four pupils in the senior secondary schools in Kenema city during the 2014/2015 academic year and a sample 165 respondents from five selected senior secondary schools made up the sample. Simple random sampling technique was used to select the five senior secondary schools. Stratified sampling was used to ensure that students from various forms and streams were equally represented in the sample. Semi structured questionnaires were developed for both teachers and pupils. The study revealed that many senior secondary schools in Kenema city needed more trained and qualified mathematics teachers than what was available. It was also found out that the necessary support to schools in terms of teaching and learning materials, incentives to mathematics teachers were grossly inadequate. Moreover, many pupils in the senior secondary schools seemed disinterested in mathematics. Some mathematics teachers had the habit of missing their teaching periods and most of those who missed their classes never compensated for the loss. Child Centered Teaching Techniques were seldom used by the mathematics teachers which might have resulted in the students’ low participation during mathematics lessons. In this digital age, none of the mathematics teachers used ICT affordable to enhance learning in the sampled senior secondary schools. Furthermore many of the senior secondary schools were located in residential areas and the classrooms were generally over crowded. In order to overcome these challenges, senior secondary school authorities, NGOs, as well as government should provide teaching and learning materials, incentives and training opportunities for mathematics teachers. Mathematics teachers should encourage pupils to be more interested and committed to the learning of Mathematics.