In recent years, several data-driven methods have been developed to help undergraduate students during course selection and sequencing. These methods tend to utilize the whole set of past course registration data, regardless of the past students' graduation GPA and time to degree (TTD). Though some previous work has shown through the results of their developed models that students of different GPA tend to take courses in different sequence, the actual analysis of the degree plans and how/if they relate to the students' graduation GPA and time-to-degree has not received much attention. This study analyzes how the student's academic level when they take different courses, as well as the pairwise degree similarity between pairs of students relate to the students' graduation GPA and TTD. Our study uses a large-scale dataset that contains 25 majors from different colleges at the University of Minnesota and spans 16 years. The analysis shows that TTD is highly correlated with both the timing and ordering of courses that students follow in their degree plans, while the correlation between graduation GPA and the course timing and ordering is not as high. We also perform a case study that uses course timing and ordering features to predict whether the student at each semester will graduate on-time or overtime. The results show that careful curriculum planning is needed to improve graduation rates in universities.