The prevalence of personal health data from wearable devices enables new opportunities to understand the impact of behavioral factors on health. Unlike consumer devices that are often auxiliary, such as Fitbit and Garmin, wearable medical devices like continuous glucose monitoring (CGM) devices and insulin pumps are becoming critical in diabetes care to minimize the occurrence of adverse glycemic events. Joint analysis of CGM and insulin pump data can provide unparalleled insights on how to modify treatment regimen to improve diabetes management outcomes. In this paper, we em- ploy a data-driven approach to study the relationship between key behavioral factors and proximal diabetic management indicators. Our dataset includes an average of 161 days of time- matched CGM and insulin pump data from 34 subjects with Type 1 Diabetes (T1D). By employing hypothesis testing and association mining, we observe that smaller meals and insulin doses are associated with better glycemic outcomes compared to larger meals and insulin doses. Meanwhile, the occurrence of interrupted sleep is associated with poorer glycemic outcomes. This paper introduces a method for inferring disrupted sleep from wearable diabetes-device data and provides a baseline for future research on sleep quality and diabetes. This work also provides insights for development of decision-support tools for improving short- and long-term outcomes in diabetes care.