This study sought to investigate the influence of head teachers’ instructional leadership practices on pupils’ learning outcomes/expectations in public primary schools in Narok North Sub-County, Kenya. This was specifically addressed by seeking to establish the influence of instructional supervision and motivational strategies on pupils’ learning outcomes/expectations in public primary schools in Narok North Sub-County, Kenya. The study employed the descriptive survey design. The target population constituted 54 public primary schools in Narok North Sub-County presented by 54 headteachers and 100 grade 5 teachers. Random sampling design was used to sample 129 respondents (45 head teachers and 84 teachers) from the target population. The descriptive analysis was used to establish the perceived level of head teachers’ instructional supervision, motivational strategies and pupils’ learning outcomes. Multiple Linear regression analysis was used to establish the influence of head teachers’ instructional supervision, motivational strategies and resource provision on the pupils’ academic performance and if the influences explained was statistically significant. Multiple Linear regression analysis was used to establish the influence of head teachers’ instructional supervision and motivational strategies on the pupils’ academic performance and if the influences explained was statistically significant. The study revealed that headteachers’ instructional leadership practices consisted of classroom visitation, delegation of teaching duties, evaluation of records of work, holding conferences with teachers, lesson preparations and evaluation of pupils’ exercise books which considerably improved the learning outcomes of grade 5 Pupils in all the five subjects. Finally, the study recommended that Re-engineering workshops by the Ministry of Education should emphasize on curriculum instructional supervision leadership practices and learners’ motivational strategies with a view to improving the quality of Grade 5 Pupils’ learning outcomes in all the five subjects’ areas.