Background and Objective: Teaching clinical skills to undergraduate medical students has brought significant challenges during the COVID-19 pandemic. Patient discussion utilized hypothetical cases from history taking to diagnosis and management. Further, everything was delivered online. Target-Oriented Clinical Skill Enhancement (TOCSE) is a teaching and learning tool that integrates the basic medical sciences, such as anatomy, physiology, pathology, microbiology, and pharmacology, at the clinical level. TOCSE has been proven to improve the clinical performance of fourth-year medical students. However, clinical confidence remains an issue, especially for medical students on pure online mode of learning during the pandemic. Therefore, this study was undertaken to determine if TOCSE also facilitates the development of confidence in the clinical performance of 4th-year medical students during the first-time patient encounter after online undergraduate classes. Methods: Eight-item Clinical Performance Confidence Scale survey was performed at three (3) time points of fourth-year medical student’s rotation in the Department of Medicine: (1) prior to the deployment to the outpatient department (Pre-OPD), (2) after the first-time patient encounter without TOCSE workshop (Post-OPD no TOCSE), and (3) after the patient encounter with TOCSE workshop (Post-OPD with TOCSE). Mean and standard deviations were used to summarize the confidence level of the 4th-year medical students, based on the 10-point differential scale being 0 as not confident at all and 10 as very confident. Wilcoxon Signed Rank assessed improvements of confidence level from Pre-OPD to Post-OPD. Effect sizes were also calculated to compare the improvement in the items. All statistical tests were performed in SPSS version 26.0. P-values less than 0.05 indicate a significant increase in the confidence level of 4th-year medical students. Results: There is a significant increase in the clinical confidence of 4th-year medical students from Pre-OPD to Post-OPD no TOCSE (mean ± SD: 6.32 ± 1.02 to 7.06 ± 0.95, p<0.001). Comparing the eight items between Pre-OPD and Post-OPD with no TOCSE, performing a complete physical examination has the most remarkable improvement. Further, there is a significant increase in the clinical confidence of 4th-year medical students from Post-OPD no TOCSE to Post-OPD with TOCSE (mean ± SD: 7.06 ± 0.95 to 7.51 ± 0.89, p<0.001). The performance of a complete history-taking has the most considerable improvement (7.29 + 1.03 to 7.89 + 1.01, p<0.001). Correspondingly, the most significant increase in the clinical confidence of 4th-year medical students was seen among the Post-OPD with TOCSE compared to their Pre- OPD confidence scores (mean ± SD: 6.32 ± 1.02 to 7.51 ± 0.89, p<0.001). Among the eight items between Pre-OPD and Post-OPD with TOCSE confidence scores, the item on performing a complete physical examination has the most remarkable improvement (5.67 ± 1.37 to 7.20 ± 1.22, p<0.001), closely followed by performing a complete history-taking (6.53 ± 1.19 to 7.89 ± 1.01, p<0.001). The most significant improvements in clinical confidence were seen in all the items in the Post-OPD with TOCSE than in the Post-OPD with no TOCSE versus Pre-OPD confidence scores. In addition, with TOCSE, the number of medical students who scored 7.50 and above was amplified more than 3 times (17.4% to 58.7%, p<0.001, Pre-OPD vs. Post-OPD with TOCSE, respectively). Conclusion: Target-Oriented Clinical Skill Enhancement (TOCSE) effectively builds up confidence during first-time patient encounters among fourth-year medical students taught online with hypothetical cases during their undergraduate classes. Key words: Target-Oriented Clinical Skill Enhancement, clinical confidence, clinical skill, fourth-year medical students, medical undergraduate challenge, online teaching in COVID-19 pandemic