As the steps of globalization accelerate, learning foreign languages has become a modern challenge for everyone. Obtaining a broad range of learning and practice material will boost the efficiency of language learning, and the Web serves as a rich source of text material. We offer methods for algorithmically creating test items that may meet needs of individual learners and instructors of English. At the current stage, we explore the generation of test items for students? practicing listening cloze in English, using text material obtained from the Web. Relying on the text corpus, a voice-synthesizer software, and linguistics-based criteria, our system identifies candidate sentences and selects distractors for composing test items for listening cloze. Teachers can select and compose the machine-generated items as they wish, and allow students to practice the composed items. In addition, the current system records histories of the performance of individual student, so the resulting system paves our way to adaptively supporting students? activities for polishing their competence in listening English.