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Background: Predicting difficult direct laryngoscopies remains challenging and improvements are needed in preoperative airway assessment. We conceived two new tests (the upper airway angle and the glottic height) and assessed their association with difficult direct laryngoscopies as well as their predictive performance. Methods: A prospective cohort was conducted with 211 patients undergoing general anesthesia for surgical procedures. We assessed the association between difficult laryngoscopies and modified Mallampati Test (MMT), Upper Lip Bite Test (ULBT), Mandibular Length (ML), Neck Circumference (NC), Mouth Opening (MO), Sternomental Distance (SMD), Thyromental Distance (TMD), Upper Airway Angle (UAA), and Glottic Height (GH). We also estimated their predictive values. Results: Difficult laryngoscopy was presented by 12 patients (5.7%). Six tests were significantly associated with difficult laryngoscopies and their area under the ROC curve, and 95% CIs were as follows: UAA = 88.82 (81.86–95.78); GH = 86.43 (72.67–100); ML = 83.75 (72.77–94.74); NC = 79.17 (64.98–93.36); MO = 65.58 (45.13–86.02); and MMT = 77.89 (68.37–87.41). Conclusion: We have found two new features (the UAA and the GH) to be significantly associated with the occurrence of difficult direct laryngoscopies. They also presented the best predictive performance amongst the nine evaluated tests in our cohort of patients. We cannot ensure, however, these tests to be superior to other regularly used bedside tests based on our estimated 95% CIs.