Monitoring the control of persons with type 1 diabetes based on their history of blood glucose levels is essential for self-management. Persons with diabetes must keep their blood glucose levels in a very narrow glycaemic region (70–180 mg/dl) to avoid hypoglycaemia and hyperglycaemia. An extended period of time in the hypoglycaemic or hyperglycaemic region can lead to short-term and long-term complications, respectively. Many measures have been proposed for the management of diabetes, such as the Glucose Management Indicator (GMI) and the Average Daily Risk Range (ADRR). A major drawback of these measures is that they only address acute (ADRR) or chronic (GMI) complications and provide no information on the trend. This paper proposes a rolling window to calculate ADRR and GMI. Calculating ADRR and GMI using a rolling window results in new data, which provide information on the efficacy of self-management of an individual and their risk trend. Use of a rolling window for the risk analysis provides novel information about the glycaemic variability and can be used for improved personal diabetes management plans. Furthermore, ADRR and GMI are combined to propose four new risk levels, which represents the lowest to the highest probable risk of complications. The analysis was performed on 12 subjects from the OhioT1DM data set. The results presented include a detailed examination and summary of all risks to the subjects and the information about their ADRR and GMI trend.