[3] Assessor began his racecourse career in a maiden race over seven furlongs on good to soft ground at Kempton Park on 7 August in which he was ridden by the apprentice jockey Richard Perham and won by three and a half lengths from Flight Lieutenant.
[5] The colt ended his season in the Group 1 Racing Post Trophy over one mile at Doncaster Racecourse in which he ran third behind Seattle Rhyme and Mack The Knife.
[6] Assessor's win at Lingfield established him as a contender for the 1992 Epsom Derby and on 2 June he started the 9/1 joint third favourite in an eighteen-runner field for the 213th running of the race.
After a break of two and a half months Assessor was ridden by Reid when he finished third to Bonny Scot in the Great Voltigeur Stakes at York and then ran sixth behind the filly User Friendly in the St Leger at Doncaster.
Three week later he returned to Longchamp for the Group 1 Prix Royal-Oak over 3100 metres on soft ground, a race which saw him matched against older horses for the first time.
He took the lead in the straight but was overtaken and beaten into second by the seven-year-old Drum Taps, with Turgeon, Sought Out, Arcadian Heights, Vintage Crop and Further Flight finishing behind.
[9] Nine days after his win at Doncaster Assessor contested the Irish St. Leger at the Curragh Racecourse and ran second to Vintage Crop, with Sonus, Drum Taps and Snurge in fourth, fifth and sixth.
Ridden by Reid, Assessor turned into the straight in fourth place, went to the front 300 metres from the finish, and pulled clear to win "easily" by six lengths.
[10] On his last run of the year Assessor attempted to repeat his 1992 success in the Prix Royal Oak but finished fifth to Raintrap after being badly hampered approaching the straight.
After coming home fifth to Sunshack in the Prix Royal Oak he was sent to Italy for the St Leger Italiano over 2900 metres at Turin of 1 November.