Many challenges are identified when students solve mathematic problems especially in solving probability word problems. This study was conducted to identify the major challenges faced by matriculation college students while solving the probability of an event word problem. Seven matriculation college students were the sample for this case study. Clinical interviews were employed as data collection. This data collection technique was selected based on the researcher's observation on the participants as they answered the task. The probability word problem task was given during the interview session. Semi-structured interviews are used to obtain in-depth information. The think-aloud analysis involves observations leading to individual behaviours in the oral or nonverbal form of participants and the researcher's field notes. Participants were found to have difficulty interpreting probabilities. Three categories of difficulties were identified, unfamiliar with the meaning of the word, not well versed in the nature of the probability, and unable to identify the goal of the probability word problem. The implication of this study can contribute ideas to instructors in developing the pedagogical techniques practiced in probability word problems.