[2] Kelly Kip was trained throughout his career by H. Allen Jerkens who was voted Eclipse Award for Outstanding Trainer in 1973 when his horses Onion and Prove Out both defeated Secretariat.
[6] He failed to reproduce his earlier form as he finished seventh of the eight runners behind Smoke Glacken, leading Jerkens to suggest that the distance of the race had been beyond the limits of his horse's stamina.
He was also beaten favorite on several occasions in the first half of the year which Jerkens explained by noting that Kelly Kip had knee problems and was not "the soundest of horses".
[11] At Laurel Park Racecourse in July, Kelly Kip was a last minute entry for the De Francis Memorial Dash, the second most valuable sprint of the season.
Carrying the high weight of 122 pounds, he turned back a strong early challenge from Richter Scale and won by three lengths from Trafalgar.
[13] In the following month, Kelly Kip finished unplaced behind Affirmed Success in a highly anticipated race for the seven furlong Vosburgh Stakes.
[15] Kelly Kip was less successful in 2000, but showed some good form in defeat when finishing second by a head when attempting to win a third Bold Ruler Handicap.
[3][16] Kelly Kip began his career as a breeding stallion at Meadowbrook at Ocala before moving to Highcliff Farm, near Delanson, New York in 2002.