1992: three-year-old season

Trained by Clive Brittain, User Friendly made her racing debut on 24 April 1992 in England with a win in the Forte Airport Service Fillies Maiden Stakes at Sandown Park Racecourse. She followed up with a win in the Lingfield Oaks Trial then on 6 June won the Group One Classic, The Oaks. On 11 July User Friendly won her second straight Group One event, taking the Irish Oaks at the Curragh.^[1] On 19 August she won the Yorkshire Oaks at York Racecourse and then on 12 September at Doncaster Racecourse she made it four Group Ones in a row and her second English Classic win by defeating her male counterparts in the St. Leger Stakes.^[2] On 4 October User Friendly was sent to Longchamp Racecourse in Paris for the prestigious Prix de l'Arc de Triomphe where she finished second to Subotica.^[3] In her last start of 1992, User Friendly was sent to Tokyo, Japan to compete in the Japan Cup in which she finished sixth to winner, Tokai Teio.

User Friendly's 1992 performances earned her two Cartier Racing Awards for, one for European Champion Three-Year-Old Filly and the other as the European Horse of the Year.

1993: four-year-old season

User Friendly made her first start at age four on 3 June 1993 at Epsom Downs, finishing fourth in the Coronation Cup. She returned to her winning form on 4 July with a victory in the Grand Prix de Saint-Cloud at Saint-Cloud Racecourse in France. On 24 July she ran fourth behind winner Opera House in the King George VI & Queen Elizabeth Diamond Stakes at Ascot Racecourse^[4] and then was third as the returning champion in the Yorkshire Oaks. On 3 October User Friendly returned to Longchamp Racecourse in Paris for the 1993 Prix de l'Arc de Triomphe. This time, she finished twenty-second in a field of twenty-three behind winner, Urban Sea.

1994: five-year-old season

In 1994, User Friendly's handlers decided to send her to compete in the United States. For trainer Rodney Rash, on 29 July she made her first start of the year winning a 1 1/16-mile Allowance race on grass at Del Mar Racetrack in California.^[5] Her next race, and the last of her career, came on 29 August at Arlington Park in Chicago. In a field of eight fillies and mares, she ran last in the Grade 1 Beverly D. Stakes behind fellow European filly Hatoof.