On May 12, 1917, Kalitan's owner, Edward R. Bradley, entered the horse in the 42nd running of the Preakness Stakes in a capacity field of 14 stakes winning colts. That race drew a full field even though it was held on the same day as the Kentucky Derby that was won by Omar Khayyam. The Preakness and Kentucky Derby were held on the same day again on May 13, 1922.
Breaking from post position five, Kalitan started at odds of 10-1 under jockey Everett Haynes and settled in third behind leader Fruit Cake and Jock Scot passing the grand stand for the first time. Then Kalitan went to the front with an early rush down the backstretch, leading at the half in 48-1/5. Around the far turn, he drew away and won by two lengths, easing up prior to the finish.