The number of COVID-19 (Coronavirus Disease of 2019) cases in Jordan is rising rapidly. A serious threat to the healthcare system appears on the horizon. Our study aims to evaluate preparedness of Jordanian frontline doctors to the worsening scenario. It has a questionnaire-based cross-sectional structure. The questionnaire was designed to evaluate preparedness according to knowledge about virus transmission and protective measures, adherence to protection guidelines, and psychological impacts affecting doctors. Institutional factors affecting doctors' readiness like adopting approach protocols and making protection equipment available were investigated; 308 doctors from different healthcare facilities participated (response rate: 53.9%). Approximately 25% of doctors (n = 77) previously took care of COVID-19 patients, and 173 (56.2%) have institutional COVID-19 approach protocols. Only 57 doctors (18.5%) reported all PPE (Personal Protective Equipment) available. The self-reported score of preparedness to deal with COVID-19 patients was 4.9 +/- 2.4. Doctors having institutional protocols for dealing with COVID-19 cases and those with sustained availability of PPE reported higher scores of preparedness (5.5 +/- 2.3 and 6.2 +/- 2.1 with p < 0.001, respectively). Correlations with knowledge score, adherence to PPE score, and psychological impacts were investigated. The study revealed multiple challenges and insufficiencies that can affect frontline doctors' preparedness. Policy makers are urged to take these findings into consideration and to act promptly.