Background: We have previously demonstrated that high-risk obstructive sleep apnea (HR-OSA), based on a modified Berlin Questionnaire (mBQ), is linked to worse clinical outcomes. Chest computed tomography (CT) imaging with the implementation of an artificial intelligence (AI) analysis program has been a valuable tool for the speedy assessment of huge numbers of patients during the COVID-19 epidemic. In the current study, we addressed how the severity of AI-guided, CT-based total opacity ratio (TOR) scores are associated with high-risk OSA and short-term outcomes in the same cohort. Methods: The ratio of the volume of high opacity areas to that of the total lung volume constituted the TOR. We arbitrarily applied thresholds of <5 (no or mild TOR), ≥5 and <15 (moderate TOR), and ≥15 (severe TOR). Results: In total, 221 patients were included. HR-OSA was observed among 11.0% of the no or mild TOR group, 22.2% of the moderate TOR group, and 38.7% of the severe TOR group (p < 0.001). In a logistic regression analysis, HR-OSA was associated with a severe TOR with an adjusted odds ratio of 3.06 (95% confidence interval [CI] 1.27–7.44; p = 0.01). A moderate TOR predicted clinical worsening with an adjusted hazard ratio (HR) of 1.93 (95% CI 1.00–3.72; p = 0.05) and a severe TOR predicted worsening with an HR of 3.06 (95% CI 1.56–5.99; p = 0.001). Conclusions: Our results offer additional radiological proof of the relationship between HR-OSA and worse outcomes in patients with COVID-19 pneumonia. A TOR may also potentially indicate the individuals that are at higher risk of HR-OSA, enabling early intervention and management strategies. The clinical significance of TOR thresholds needs further evaluation in larger samples.