Despite his pedigree, he failed to attract a bid at the 2006 New York Breeders Sale at Saratoga possibly because his sire had yet produced anything notable since the multiple graded stakes winner Isitingood in 1991, or possibly because Tin Cup Chalice was small and narrow and had come too near death too often to inspire confidence.

To take the Albany and with it the Triple Crown of New York-breds, Tin Cup Chalice had to step up in class.

I wouldn’t bet against a horse that’s undefeated.”[1] In the Albany Stakes, ridden by regular jockey Pedro Rodriguez, he defeated Icabad Crane and Big Truck, both New York-breds and both recently off the United States Triple Crown of Thoroughbred Racing trail.

In his first start outside New York and in graded stakes company, Tin Cup Chalice won the Indiana Derby.

[3] While Pedro Rodriguez has been the regular rider for Tin Cup Chalice, and was to travel to Japan, he encountered Visa/Passport issues and was not successful in obtaining a permit.

[4] On April 17, 2009, while in training at Finger Lakes Gaming and Race Track, Tin Cup Chalice suffered a spinal injury in the head-on collision with a runaway colt named Zany, a 4 year old son of War Chant at about 6:20 am EST.

Despite more than 90 minutes of care and treatment on the track, the decision was made to euthanize Tin Cup Chalice when it became apparent to veterinarian Brendan Warrell that the injuries were catastrophic.

"[7] Tin Cup Chalice was transported to Cornell University's equine hospital for a necropsy, part of insurance requirements.