In his first track season at age 16, Boldon finished with 21.20 seconds in the 200 metres and 48.40 seconds in the 400 metres, recording a double win at the Queens County Championships in 1990, and earning MVP honours. After transferring for his final year from Jamaica High to Piedmont Hills High School in San Jose, California, Boldon was selected to the San Jose Mercury News' Santa Clara all-county soccer team. He also continued to sprint, placing third in the 200 m at the CIF California State Meet in 1991. Athletics became his primary focus and he won the Junior Olympic Title that summer in Durham, North Carolina, in 200 m.