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CH Sky Watch was foaled on June 14, 1977 at Earl Teeter and Sons Farm in Lexington, Ky. He was bred by Della Large of Chicago. He was sired by Flight Time, a son of the immortal Wing Commander out of Aries Golden Gift by Genius Bourbon King. CH Sky Watch began his early training with Mitch Clark and initial plans were to show CH Sky Watch pulling a cart rather than under saddle. The horse did not take to being harnessed and it was decided he should be trained under saddle instead. CH Sky Watch made his show ring debut in Louisville, Ky. in 1979, winning the World's Champion Two-Year-Old Five-Gaited Stake.

Michelle MacFarlane saw CH Sky Watch show as a two-year-old, purchasing him for $50,000 and sending him to California to be trained by Rob Tanner. As a three-year-old, CH Sky Watch finished fourth in both the World's Championships and the National Futurity. As a four-year-old, CH Sky Watch returned to trainer Mitch Clark and went on to win the World's Champion Junior Five-Gaited Horse title in 1981.

In 1982, the infamous CH Imperator and CH Sky Watch duels began. CH Sky Watch won every World's Champion Five-Gaited Stallion Stake at Louisville from 1982 through 1985 and again in 1988. CH Imperator was a gelding and won every World's Champion Five-Gaited Gelding Stake in Louisville from 1979 through 1988 except for two. Beginning in 1982 these two horses would face off in the World's Grand Champion Five-Gaited Stake four times. In their final battle in 1988, Michelle MacFarlane rode CH Sky Watch in the World's Grand Champion Five Gaited Stake for the first time. CH Sky Watch would eventually win the class and Michelle would become the only woman amateur in history to win the coveted title.

CH Sky Watch ended his career with four World's Grand Championships (1982, 1983, 1984, and 1988), and twelve World titles in all. He stood stud in 1989 at MacFarlane's Scripps Miramar Ranch in California. After the death of CH Sky Watch’s rival, CH Imperator in 1997, MacFarlane felt that CH Sky Watch would a worthy replacement at the Kentucky Horse Park’s Hall of Champions. In 1998, Sky Watch became a resident at the Kentucky Horse Park's Hall of Champions while still an active breeding stallion. He was humanely euthanized on April 22, 2001 due to infirmities at the age of 24. He is buried at the Hall of Champions.