He was bred by Thomas McDowell at his Ashland Stud in Lexington, Kentucky. He was the son of the 1895 Kentucky Derby winner Halma.
Raced and trained by McDowell, at age two Alan-a-Dale won three of his four starts but the following year health problems kept him out of racing until Kentucky Derby time. Ridden by future Hall of Fame jockey Jimmy Winkfield, the official Kentucky Derby website says that Alan-a-Dale had a lead of six lengths and despite going lame down the stretch, "carried on with flawless courage to win by a nose."