Boland's debut came in 1961, when he competed at Daytona, trying to make his way into the Daytona 500. However, Boland literally hit a wall in the Qualifier event, finishing 27th and missing the Daytona 500. Luckily, he recovered later that year to post a career-best 11th place start and 12th place finish at Winston-Salem.
Boland didn't reutrn to the sport until 1964, when his three-race schedule put him 116th in points. Boland did struggle for the better part of the year, failing to finish any of his races, including last place finishes at Islip (22nd) and Watkins Glen (26th). His best finish was just a 20th place finish in a twenty-one car field at New Oxford, his final career start.