Driver Eric Ledford won in his Hambletonian debut as Chip Chip Hooray trotted the mile in one minute, 53.3 seconds and Chuck Sylvester became the fourth trainer to condition four Hambletonian winners.
Andover Hall, the 2-1 favorite, buckled on the first turn and did not finish.
Chip Chip Hooray, who went off at 4-1, paid $12.60, $9.00 and $8.40. Like a Prayer returned $17.40 and $11.20 and Duke of York showed for $10.40.
"He's a little big horse," Sylvester said after adding to his place in trotting history. Ben White, Stanley Dancer and Bill Haughton are the only other trainers with four Hambletonian winners, each having won five times.
Andover Hall's problems came after making contact with Likely Lad. The collision cut Andover Hall's left hind leg and the horse pulled up before the finish line with the help of an outrider.
"We just got jammed up in traffic on the first turn and my horse lost stride," said Andover Hall driver John Campbell, who has won this race five times.
But the result was not surprising to Sylvester, especially since Chip Chip Hooray beat Andover Hall in one of three elimination races last week, when the Hambletonian field was cut from 25 horses to 10.
"I was surprised they made Andover Hall such a big favorite," Sylvester said. "I thought we won a big race last week."
Starting from the second post position, Chip Chip Hooray stayed in the middle of the field in the first half of the race and moved into contention near the final turn.
"We didn't want him to be going too fast. We were just trying to bide our time," Ledford said.
When pacesetter Taurus Dream weakened in the stretch, Chip Chip Hooray moved to the lead in the middle of the track and appeared to be on his way to victory with a two-length advantage.
However, Ron Pierce rallied Like A Prayer and finished just a neck behind Chip Chip Hooray.
"He raced great," Like a Prayer trainer Brett Pelling said. "He raced barefoot today and responded well. I was happy with his performance."
Duke of York edged Malabar Maple for third place.
Windylane Hanover, a 25-1 longshot, won the Hambletonian Oaks for fillies in 1:53, finishing two lengths ahead of 7-2 choice Cameron Hall.
Windylane Hanover, driven by Pierce, followed Cameron Hall in a loose pocket, moved clear at the top of the stretch and outsprinted her to the finish.
"We got lucky with a soft path and she had a lot of kick coming home," said Windylane Hanover trainer Brett Bittle.