in the Molly Pitcher Stakes at Monmouth Park on July 4, winning comfortably by eight lengths. She then shipped to Saratoga in upstate New York for the Whitney Handicap on August 6, facing male horses for the first time. The race attracted only two other horses, multiple stakes winners Gulch (Metropolitan Handicap) and King's Swan (Tom Fool Handicap). Over a sloppy track that favored front runners, Personal Ensign trailed the field by about four lengths for the first five furlongs, then started to make up ground around the turn. After completing the mile in 1:35, she got her head in front and continued to draw away, winning by lengths over Gulch. She completed the nine furlongs in 1:47. "I can now say she is the best horse I ever road," said Romero. "She ran a great race." It was her tenth win in a row, matching the streak of Ruffian before the latter filly broke down in her final start. It also moved her to the top of the NTRA polling for Horse of the Year. Personal Ensign made her next start in the Maskette Stakes over a distance of one mile at Belmont on September 10, where her main rival was Winning Colors, who had won the 1988 Kentucky Derby. Winning Colors was coming off a three-month layoff but was also carrying seven pounds less than Personal Ensign. She was also the only "speed" horse in the field, and as expected went to the early lead. She set a fast pace of 0:45 for the first half-mile, opening a large lead on the rest of the field. "When she got that far in front," said McGaughey, "I was worried." Around the turn, Personal Ensign began to close ground and trailed by just two lengths after the six furlongs was completed in 1:09. In the top of the stretch, she moved alongside Winning Colors but the other filly responded to the challenge. The two dueled for the remaining eighth of a mile until Personal Ensign finally pulled ahead in the final strides to win by three-quarters of a length. "They both made me proud today, especially my filly," said Romero. "A mile isn't even her best distance. I just let her run her race and knew she would get the job done." On October 16, Personal Ensign entered the Beldame Stakes to defend her victory in the previous year's race.