(1) Background: The present study aimed to assess the changes in blood pressure (BP) within the first 6 months of treatment initiation in a newly treated hypertensive cohort and to identify the factors that are associated with achieving the target BP recommended by the American (ACC/AHA, 2017), European (ESC/ESH, 2018), United Kingdom (NICE, 2019), and International Society of Hypertension (ISH, 2020) guidelines. (2) Methods: We analyzed 5308 incident hypertensive outpatients across Abu Dhabi, United Arab Emirates (UAE), in 2017; each patient was followed up for 6 months. Hypertension was defined as a BP of 130/80 mmHg according to the ACC/AHA guidelines and 140/90 mmHg according to the ESC/ESH, NICE, and ISH guidelines. Multiple logistic regression was used to identify factors associated with achieving the guideline-recommended BP targets. (3) Results: At baseline, the mean BP was 133.9 ± 72.9 mmHg and 132.7 ± 72.5 mmHg at 6 months. The guideline-recommended BP targets were 39.5%, 43%, 65.6%, and 40.8%, according to the ACC/AHA, ESC/ESH, NICE, and ISH guidelines, respectively. A BMI of <25 kg/m2 was associated with better BP control according to the ACC/AHA (odds ratio (OR) = 1.26; 95% confidence interval (CI) = 1.07–1.49), ESC/ESH (OR = 1.27; 95% CI = 1.08–1.50), and ISH guidelines (OR = 1.22; 95% CI = 1.03–1.44). Hypertension treated in secondary care settings was more likely to achieve the BP targets recommended by the ACC/AHA (1.31 times), ESC/ESH (1.32 times), NICE (1.41 times), and ISH (1.34 times) guidelines. (4) Conclusions: BP goal achievement was suboptimal. BP control efforts should prioritize improving cardiometabolic goals and lifestyle modifications.