A number of research projects in educational assessment reveal that students struggle when it comes to accomplishing problem-solving tasks in Mathematics. Such a struggle is primarily due to the complexities of problem-solving. Students deal with these struggles by employing mechanisms that could be classified into either problem-focused or emotion-focused coping strategies. The study was implemented through a design-research approach by using a model-building framework with four stages: 1) analysis; 2) development; 3) implementation/validation; and 4) evaluation. The models with the two variables were also linked to the student’s sexual orientation and academic programs. Through descriptive statistical measures, such as frequency count and percentages, difficulties were enumerated through the administration of a problem- solving test. It should be noted, however, that a respondent may have at least one difficulty in the different phases of problem-solving. Two hundred and ninety-seven of the 425 college respondents were involved in the model-development stage. The majority of both males and females experienced the same difficulty/ies in all the phases, namely; the inability to distinguish the known from the unknown information (U1), the inability to transform a problem into a mathematical equation (D1), the inability to completely perform the working procedure systematically and accurately (C1), and the inability to start the evaluation of the correctness of the obtained solution (L2). The majority of the respondents of both the STEM-related and non-STEM-related academic programs experienced the same difficulties, namely: D1, C1 and L2 in the DP, CP and the LB problem-solving phases, respectively. In the UP phase, however, the majority of the respondents in the STEM-related academic programs experienced U2, and U1 for the non-STEM-related academic programs. Moreover, 43 acts of coping were elicited from the respondents through a coping-strategy questionnaire, 32 of which were classified as problem-focused, whereas 11 were categorized as emotion-focused. Both sexes utilized the coping strategies: UP2, DP8 and CP7 in the phases of UP, DP and CP respectively. In the LB phase, LB3 was utilized by the males and LB1 was utilized by the females. The majority of the respondents of the STEM-related academic programs preferred UP2, DP8, CP7 and LB1 coping strategies, while UP2, DP8, CP7 and LB3 opted for the non-STEM related academic program respondents. The identified relationships between and among the variables brought forth two models namely: Coping Strategy by Sex by Phase, and Coping Strategy by Academic Program by Phase. Purposive sampling factors, like the availability of the respondents and the matching of coping strategies, as presented in the models developed were taken into consideration in evaluating the effectivity of the models. From the sampled respondents in the validation group, where the frequency of their pre-identified difficulties had either decreased or were totally resolved. The study concludes that the models have the ability to address the difficulties of the students in their problem-solving encounters through their coping strategies. Therefore, this study recommends that teachers should provide students with problem-solving tasks that focus on the phases in which they struggle. Additionally, this study encourages teachers to allow their students to apply their most-preferred coping strategies, so that they could perform better in Mathematics problem-solving.