The number of attempts to provide students is a key instructional characteristic in computer-based learning (CBL). However, it has not been covered extensively, and there is a need to delve deeper into the factors affecting multiple-try performance and allowing its successful use, including the learner’s involved emotional processes. This study examines the effects of multiple-try on a drill-and-practice mathematical game devoted to primary school students. A total of 73 students from four courses from two schools participated in the experiment. They were randomly assigned to a 3-attempt multiple-try (MTF) and a single-try knowledge of correct response (KCR) conditions. The study covered impacts on learning performance, together with motivation, effort, pressure, and the value of students regarding the learning activity based on the self-determination theory (SDT) perspective and its cognitive evaluation sub-theory (CET). The study’s main findings were that (a) the MTF condition outperformed KCR in terms of students’ learning gains; (b) MTF presented higher levels of perceived competence and autonomy, which, according to SDT, fosters motivation and learning; (c) a cost was yielded in students’ perceived pressure under MTF; and (d) perceived effort and value was similarly high for both conditions despite learning differences. This study complements the existing literature on multiple-try, providing insights into what conditions are beneficial for multiple-try use.