Objectives This study aimed to assess the knowledge of and willingness for dispensing oral anticancer drugs (OADs) among community pharmacists in Jordan. Methods A cross-sectional survey was conducted among pharmacists in community pharmacies. Key findings Five hundred pharmacists completed the questionnaire. The mean age of respondents was 30.4 ± 6.2 years (range 21–61). Most pharmacists had a bachelor’s degree in pharmacy (80.8%) and were staff pharmacists (61.6%). Two hundred and ten (42.0%) pharmacists indicated not receiving adequate education on OADs at the undergraduate level. The majority of respondents (79.8%) did not attend continuing education events in oncology in the past 2 years. Further, 44.6% of pharmacists never dispensed OADs in their pharmacies. The mean score of knowledge of OADs was 1.7 ± 1.9 out of 12 points (range 0–9). The vast majority of pharmacists surveyed (97.6%) had poor knowledge of OADs. Almost half of the pharmacists (49.8%) agreed or strongly agreed to be comfortable answering questions regarding cancer treatments. More than half of respondents (52.2%) feel comfortable providing patient education on OADs. Half of the respondents (49.6%) disagreed that their current pharmacy settings are equipped with the necessary tools to handle OADs. Conclusions A large number of community pharmacists in Jordan lack the foundational knowledge regarding OADs. A substantial proportion of pharmacists never dispensed OADs and were not satisfied with the level of undergraduate education received regarding oncology and oral cancer therapies. Nevertheless, most pharmacists were willing to handle OADs and were positive about receiving further training/education on dispensing OADs. Collectively, efforts are needed to improve pharmacy education on oral chemotherapy and cancer care along with continuous training for pharmacists in their community settings.