Nahem began racing Bertrando in a three-way partnership with Marshall Naify's 505 Farms of Lexington, Kentucky, and Gus Headley, son of the horse's trainer, Bruce Headley. En route to being voted California Champion two-year-old colt, Bertrando won the important Del Mar Futurity and the Grade INorfolk Stakes, one of the final preparatory races for two-year-olds going into the Breeders' Cup Juvenile. In that race, the most important of the year, Bertrando broke quickly and took an early lead. Then, from the back of the 14-horse field, the French colt Arazi began making a move. In what a 2006 National Thoroughbred Racing Associationarticle called "the single-most spectacular performance in Breeders' Cup history", Arazi wove between horses and with two furlongs to run passed Bertrando to win.
Racing in California in 1992, the three-year-old Bertrando won the San Felipe Stakes and was second to A.P. Indy in the Santa Anita Derby. As a result of a respiratory systemvirus, the colt did not compete in any of the U.S. Triple Crown races. While Bertrando was sidelined for several months, Gus Headley was bought out of the partnership, and Robert J. Frankel took over as Bertrando's trainer. Near the end of the year, Bertrando returned to compete in the Malibu Stakes, finishing third. Although his 1992 performances were limited, he earned California Champion three-year-old colt honors.
Following arthroscopic surgery on a knee, Bertrando returned to race again at age five. He won the 1994 Wickerr Stakes and Goodwood Breeders' Cup Handicap. In his third attempt to win a Breeders' Cup race, he entered the 1994 Classic, where he finished sixth. After two unplaced showings in 1995, Bertrando was retired to River Edge Farm in Buellton, California, where he became a successful sire of a number of stakes-race winners. Bertrando is a direct sire-line descendant of Man o' War through his son War Relic.
He died from infirmities of old age on March 27, 2014.