This study is an exploratory study aiming to add to the scarce research exploring the enhancement of 21st century skills across the undergraduate years of Education student. Data were collected from 329 undergraduates (96% females), who learned at Ashkelon Academic College, Israel. 103 students (31%) were at the beginning of the freshman year, 102 students (31%) were at the end of the second school year, and 123 students (38%) were at the end of the graduation and final school year. The 21st century skills were assessed using a 32 Likert-type item questionnaire about 21st century skills. Results indicated of positive relations between all 21st century skills, and between undergraduates` matriculation examination grades and all these skills, except for ICT. Significant differences in 21st century skills were found between freshman year and advanced years. 21st century skills mastery was higher in advanced years compared to freshman year. Educational implications are discussed.