The Derby winner, Brokers Tip, finished last in the field of ten. Tom Hayes had taken over as the trainer for the new owner after the Derby and the Preakness win with Head Play marked his second win in the event, having won in 1897 with the colt Paul Kauvar. Only a few months after, Hayes died on August 28, 1933 at his home in Lexington, Kentucky. Head Play was injured and did not win another race in the remainder of his three-year-old or four-year-old seasons. As a five-year-old, he came back into form from his injury and won four stakes races on separate coasts of the country. Early in 1935, he won both the inaugural running of the San Antonio Handicap in the first week of February at one and one eighth mile on the dirt and the San Juan Capistrano Handicap in the second half of April at the same distance at Santa Anita Park outside Los Angeles in California. Then he won the Bay Meadows Handicap at one and one eighth miles in the San Francisco Area in Northern California at Bay Meadows Racetrack. In May, he ran against the 1934 Kentucky Derby winner, Cavalcade, at Belmont and recorded an upset victory over the younger horse. On the fourth of July weekend, Head Play won the prestigious Suburban Handicap at 1¼ miles on the dirt at Belmont Park in New York over Discovery with Cavalcade losing his rider at the start. He won the Derby Week Special at one and one eighth miles at Detroit in mid-June over Stand Pat and Azucar. He bowed slightly after this and never regained his form, racing only twice the next year unsuccessfully.