This research aimed at investigating the effect of two types of collaboration in designing mathematic problems on developing the depth of understanding and creative awareness of mathematical problem solving for preparatory year students who were learning mathematics. The quasi-experimental research design with a control group and two experimental groups was used in this research. 38 Students were in the control group while the experimental groups were assigned for the two types of collaboration: free collaboration )41 students( and guided collaboration )40 students(. All the participating students in the three groups were males who were registered at the mathematics course delivered in the preparatory-year program at Tabuk University. The instruments were: the scale of creative awareness of problem solving, and a rubric to measure students' ability of designing mathematic problems which was created by the researchers. The results showed that there were statically significant differences between the control group and the collaboration groups in favor of the collaboration groups on both the creative awareness of mathematic problem-solving and the ability of designing mathematic problems. In addition, the results revealed that the guided collaboration group scored higher than the free collaboration group on both the creative awareness of mathematic problem solving and on the ability of designing mathematic problems.
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