The monitoring of learning over time is critical for determining progression within and across cohorts of learners. This research investigated the use of the Rasch Measurement Model to determine the functioning of anchor items as well as an application of the model to convert the results to the same metric. A group of 321 Grade 8 learners and the same in the following school year wrote English Additional Language Comprehension Tests aimed at monitoring learning progression over years. The two tests were linked with 15 anchor items. This study examined the results of the anchor items from Years 1 and 2, applying non-parametric statistical tests as well as the Rasch Partial Credit Model to identify items which did not contribute to monitoring learning progression; these items were removed or refined based on the results and reviews by subject specialists. Learner results from Grades 8 and 9 were placed in the same frame of reference by applying the Rasch Partial Credit Model in order to establish a more accurate representation of the magnitude of learning progression. The first finding illustrated that applying non-parametric statistics and Rasch Measurement Theory identifies potentially problematic anchor items, and that when items are improved or removed, the overall results tend to be more stable and precise. Second, it was found that when applying Rasch item and threshold calibrations to assessment results, a more accurate indication of learning progression is obtained which can be used to communicate results to stakeholders and more importantly, inform teaching and learning.