- He started out racing harness horses before switching to Thoroughbreds in 1982.
- He dominated the Gulfstream Park owners’ standings between 2009-2013 before finishing second during the 2012- 2013 meet to Kenneth and Sarah Ramsey. Mr. Calabrese dominated the owner standings during Gulfstream's first summer meet.
- Dominating the Chicago circuit for more than a decade
- He enjoyed his greatest success as an owner with Dreaming of Anna, who captured the 2006 Breeders’ Cup Juvenile Fillies.
- He also campaigned her brother, Lewis Michael, who captured the 2008 Pat O’Brien (G2) and the 2007 Washington Park Handicap (G2).
- The Calabrese-owned Silver Maiden won the first five races of her career in 1997, capped with a Grade 1 score in the Frizette at Belmont.
- In recent years, Calabrese has been well represented by Romacaca, whom he claimed for $25,000 and went on to become a multiple graded-stakes winner. She won the 2012 South Beach Stakes and was third in the Sunshine Millions Filly & Mare Turf.
- The Calebrese-owned Sabrina’s Dance captured the Madcap Escapade Stakes during the 2011-12 Gulfstream meeting.