(1) Background: Regular contact with a medication therapy management (MTM) pharmacist is shown to improve patients' understanding of their condition; however, continued demonstration of the value of a pharmacist delivered comprehensive medication review (CMR) using enhanced MTM services via telehealth is needed. The study aimed to describe a pilot program designed to improve type 2 diabetes mellitus (T2DM) management through enhanced condition specific MTM services. (2) Methods: This retrospective study included patients with T2DM aged 40-75 years who received a pharmacist-delivered CMR between January and December 2018. An evaluation of glycosylated hemoglobin (HbA1c) values 3 months pre- and post-CMR was performed. Wilcoxon signed-rank and chi-square tests were used. (3) Results: Of 444 eligible patients, a majority were female (58%) with a median age of 70 years. Median HbA1c values post-CMR were lower than pre-CMR (median 7.1% range 4.5-13.6; median 7.4% range 4.5-13.9, respectively; = 0.009). There were fewer participants with HbA1c >9% post-CMR ( = 66) than pre-CMR ( = 80; < 0.001) and more with HbA1C <6.5% post-CMR ( = 151) than pre-CMR ( = 130; < 0.001). (4) Conclusion: This program evaluation highlighted the value of an enhanced condition specific MTM service via telehealth. Patients had improved HbA1c values three months after receiving a single pharmacist delivered CMR.