Tiller returned to the turf two weeks later and finished second to Noble Dancer in the San Luis Rey Handicap. On his final Californian start on April 8, Tiller started at odds of 3/1 under a weight of 126 pounds for the San Juan Capistrano Handicap. Ridden by Cordero, he raced in the first five for most of the race before moving up on the outside to take the lead in the straight and got the best of a "battling finish" to win by three quarters of a length from Exceller, with Noble Dancer in third. The gelding then returned to the East coast and won an allowance at Belmont in June, but his subsequent form was less impressive. He ran unplaced in the Suburban Handicap and the Brooklyn Handicap (both on dirt), finished third to Native Courier in the Grade III Brighton Beach Handicap, and ended his season by finishing second to Fluorescent Light in the Manhattan Handicap on September 23. After a break of more than eight months, Tiller returned to racing at Belmont and finished unplaced in allowance races in May and June. On June 29 however, he returned to winning form as he won the Tidal Handicap for a second time, beating Scythian Gold into second. On July 12 he was matched against the five-year-old gelding John Henry in the Sword Dancer Invitational Handicap at Belmont. He raced in third place as John Henry duelled for the lead with Marquee Universal before moving forward approaching the final turn. He overtook John Henry in the straight and won by a length and a quarter in a time of 2:25.4, two-fifths of a second outside Secretariat's track record. On his next appearance, the gelding finished third to Premier Ministre and Great Neck in the Bernard Baruch Handicap at Saratoga Race Course in August. On September 7 Tiller faced both John Henry and Premier Ministre in the Brighton Beach Handicap. At the 5/16 pole, Tiller broke his right hip while attempting to overtake the race leader John Henry, causing significant hemorrhaging. He was taken from the track in a horse ambulance. His trainer David Whiteley said, "We don't know what happened. Ruben (Hernandez) said he was not bumped. It was just one of those things that can happen in a race." Tiller was not euthanized immediately after the race and was able to put limited weight on the hip.