He finished unplaced in his only race as a two-year-old in 2018 but won four of his five starts in the following year and made further improvement as a four-year-old when he took the Listed Tapster Stakes and the Group 2 British Champions Long Distance Cup.
[7] After an absence of over nine months, Trueshan began his second campaign in a novice race (for horses with no more than two previous wins) over one and a half miles on the synthetic Tapeta at Wolverhampton Racecourse on 2 August.
[10] On his final run of the season Trueshan, ridden by Buick, won a conditions race at Newbury Racecourse two weeks later, getting the better of a sustained struggle with the odds-on favourite Hamish to prevail by a neck.
On his seasonal debut, Trueshan was moved up in class for the Listed Buckhounds Stakes, which was run that year at Newmarket on 7 June, and came home fourth of the ten runners, beaten just over three lengths by the winner Dashing Willoughby.
[12] At York Racecourse in August Trueshan was assigned a weight of 135 pounds for the Ebor Handicap and finished eighth behind the six-year-old Fujaira Prince after struggling to obtain a clear run in the straight.
[13] Hollie Doyle resumed her partnership with Trueshan when the gelding was stepped up to Group 2 class to contest the British Champions Long Distance Cup over two miles on soft ground at Ascot Racecourse on 17 October and started at odds of 11/1.
After racing in mid-division for most of the way Trueshan made a forward move entering the straight, gained the advantage a furlong out and drew right away in the closing stages to win "easily" by seven and a half lengths from Search For A Song.
[16] Trueshan began his fourth season in the Group 3 Ormonde Stakes over thirteen furlongs at Chester Racecourse on 6 May and finished second to the Aidan O'Brien-trained favourite Japan, beaten three-quarters of a length by the winner.
In June he was expected to contest the Ascot Gold Cup but bypassed the race as King felt that the ground would have been too firm, and was instead dropped back to handicap class for the Northumberland Plate at Newcastle Racecourse.
With Stradivarius being withdrawn on account of the soft ground Trueshan started the 6/5 favourite in an eight-runner field which included Serpentine, Santiago, Sir Ron Priestley (Princess of Wales's Stakes), Amhran Na Bhfiann (Curragh Cup).
In a race run in heavy rain Trueshan settled in mid-division as the outsider Alkuin set the pace from Bubble Smart, before moving into contention approaching the final turn.
[19] James Doyle commented "He stays all day and has a good kick on this ground as well... Hollie has been a big part of this horse's career and to miss out today through suspension is pretty tough.
"[20] Two weeks later at Ascot, with Hollie Doyle back in the saddle, Trueshan attempted to repeat his 2020 success in the British Champions Long Distance Cup and started even money favourite in a ten-runner field.