[3] However, he improved and on his third start on 9 March 1895 at Flemington Racecourse he won the VRC Unplaced Two Year Old Stakes over a distance of 6 furlongs at the long odds of 10/1 in a time of 1:171⁄2.

[6] Two weeks later Merman ran at the Old Course (renamed to Victoria Park Racecourse in 1897) in the Adelaide Stakes over 6 furlongs but was soundly defeated finishing fifth as topweight and favourite by Gehenna.

In the autumn after a fifth placing in the VRC Brunswick Stakes at Flemington the horse was taken to New South Wales and raced Randwick Racecourse in the AJC Flying Handicap and was once again unplaced.

[11] On Victoria Derby Day Merman ran in the VRC Coburg Stakes and finished fourth as the 4/1 favourite beaten by his nemesis at the time, Ayrshire.

[15] Thompson was a mentor to the horse owner and actress Lillie Langtry and after seeing the cable from Wilson she agreed to purchase the stallion through William Allison as an agent, for 1,600 guineas.

[30] Racing on the third day at Newmarket in a row, Merman spectacularly won the Jockey Club Cup over two miles two furlongs and 32 yards defeating rivals The Rush and Bay Ronald.

Merman began his season in full earnest on 19 April in the City and Suburban Handicap at Epsom Downs but he failed to fire finishing in 16th to familiar Newhaven.

[33] After an unsuccessful run in May in the Princes Handicap at York, Merman was rested and then on 23 July started as the 4/1 favourite in the Liverpool Cup at Manchester Racecourse and finished 5th.

[35] On the next day Merman's owner Lily Langtry married Hugo Gerald de Bathe in Jersey[36] and was present to witness her horse capture the prestigious Goodwood Cup over the 21⁄2 miles distance.

Merman's next venture was across the English Channel to France, where on 20 August 1899 at Deauville-La Touques Racecourse he conceded 22 pounds to the three-year-old Fourire and was valiantly beaten[38] in the 2,500 metres Grand Prix de Deauville.

[39] Returning to England, Merman next appeared in the 11⁄2 miles October Plate at Kempton Park where he was defeated into second place as the 1/3 odds on favourite by the 4 year old mare St.

[40] Five days later on 10 October 1899 Merman returned to Newmarket and started in the Cesarewitch Stakes for the third time and finished thirteenth to 6/1 lightly weighted favourite Scintillant.

[40] In his last start of the year in the Jockey Club Cup it was noted that Merman again had to concede 18 pounds in weight to Mazagan and it seemed that his form was waning and retirement was imminent.