Lonesome Glory was originally intended for a career in Show-jumping but proved temperamentally unsuitable and was switched to racing.
In December, he was sent across the Atlantic to contest the Sport of Kings Challenge, a hurdle race over 2 miles 5+1⁄2 furlongs at Cheltenham Racecourse in England.
[3] After the race, Lonesome Glory and his rider were given an enthusiastic reception by British racegoers: Miller explained that "there were a lot of people around clapping and cheering...
Ridden by Blythe Miller, he defeated the odds-on favorite Highland Bud, who was partnered by the British Champion jockey Richard Dunwoody.
[6] Lonesome Glory's most important win at age six in 1994 came in the Colonial Cup at Camden, South Carolina, in which he defeated Mistico by a head.
On November 12, he claimed his second Colonial Cup, beating Rowdy Irishman by a length and a half after taking the lead at the last fence.
He finished fourth in the Peter Marsh Chase at Haydock Park racecourse in January before a muscle injury ended his British campaign.
In April 1997, running on Lasix for the first time, he won the Carolina Cup from Hudson Bay and Prime Legacy.