During the 1909 Vanderbilt Cup Race, two other sweepstakes races (the Massapequa Sweepstakes and the Wheatley Hills Sweepstakes) were run simultaneously for commercially available stock cars.
The Massapequa Sweepstakes had six entrants for the smallest stock cars with engines 161 to 230 cubic inches. The winner received a prize of $1,000.
The 10 lap, 126.4 mile race had a small but competitive field of six entries: two Chalmers-Detroit “30’s,” one Hudson and three Maxwells. Fastest out of the gate was the #45 Maxwell of Thomas Costello, cutting a lap at 60 miles per hour. His success was short-lived as he hit a tree on his second lap and damaged the machine too severely to continue.
By that time George Ainslee in the #42 Hudson had passed Joe Matson’s #43 Chalmers-Detroit for second place and was able to move into the lead with the demise of Costello. Matson, who in June won the Indiana Trophy, a stock car race for the same class held in Crown Point, Indiana, re-passed Ainslee for the lead. He paced out the remaining seven laps steadily extending his lead to 18:30 over eventual second place finisher Martin Doorley in #46 Maxwell. Joe Matson’s winning race average was 58.4 miles per hour.
If not for a broken rear axle during the last lap on the #41 Chalmers-Detroit driven by “Buster” Brown, the Chalmers team could have finished one-two.