The difficulties in estimating the Worst-Case Execution Time (WCET) of applications make the use of modern computing architectures limited in real-time systems. Critical embedded systems require the tasks of hard real-time applications to meet their deadlines, and formal proofs on the validity of this condition are usually required by certification authorities. In the last decade, researchers proposed the use of probabilistic measurement-based methods to estimate the WCET instead of traditional static methods. In this chapter, we summarize recent theoretical and quantitative results on the use of probabilistic approaches to estimate the WCET presented in the PhD thesis of the author, including possible exploitation scenarios, open challenges, and future directions.