The COVID-19-pandemic entailed abrupt/long-lasting changes in university students’ lives, resulting in growing stress and stress-related outcomes. Although nowadays the pre-pandemic-life is gradually re-establishing, past-COVID-19-stressful experiences and strategies adopted to adjust to this condition may significantly impact students’ current experiences. Therefore, the development of research exploring the complex interplay between perceived past/present COVID-19-related experiences, coping strategies, and psychological health currently reported by students is needed. This study simultaneously tests the associations between Past-COVID-19-stressors and Current-COVID-19-stressors as moderated by Coping Strategies and the associations between Past-COVID-19-stressors and Psychological Symptoms as mediated by Current-COVID-19-stressors. A mediated-moderated model was tested on 355 university students. COVID-19-Student-Stress-Questionnaire (CSSQ) was used to assess COVID-19-stressors. Two CSSQ-versions were used, one of which was adjusted to assess Past-COVID-19-stressors recalled from previous restrictive pandemic phases. Coping-Orientation-to-Problem-Experienced-New-Italian-Version and Symptom-Checklist-90-Revised were used to assess, respectively, Coping Strategies and Psychological Symptoms. Findings confirmed the hypothesized Mediated-Moderated Model. The effects of Past-COVID-19-stressors on Current-COVID-19-stressors were moderated by Coping Strategies, and the effects of Past-COVID-19-stressors on Psychological Symptoms were mediated by Current-COVID-19-stressors. Unique psychopathological risk profiles deriving from the interplay between specific past/present stressors and coping strategies were found. Researchers and clinicians can use these findings to develop updated research and timely evidence-based interventions fostering students’ adjustment in the current period. Future research should further explore the impact of the complex interplay between perceived past/present COVID-19-related experiences and individual characteristics on psychological health conditions reported by people in the aftermath of the COVID-19 pandemic.