In this study, we developed a prototype system that helps students practice speaking English. When students speak English, they may have difficulty expressing their intentions in real time, even when they know the correct words and phrases. To think of the correct English terms smoothly, it is important that students use the language knowledge they have acquired. By using probable linguistic situations, our system attempts to check and provide information about the words and phrases learners can use. We conducted an experiment with 105 first-year Japanese university students to investigate the following research questions: (1) Does the prototype system run properly, provide questions, and save the log data as expected?; (2) When we check the learners’ answers in real time, how many evaluation items and evaluation levels are appropriate?; and (3) How should we display the results of the evaluation to ensure visual comprehension? Concerning the first question, the results of the experiment show that the system runs properly and saves the log data. For the second question, the results suggest that a few evaluation items and a few evaluation levels are preferable for checking the learners’ answers in real time. Results for the third question suggest that a color-coded table could help visually interpret the learners’ results. In this table, English sentences grouping probable linguistic situations are classified according to the percentage of the correct answers, such as less than 50%, 50?80%, and more than 80%.