Purchased for $150,000 from the Fasig-Tipton Midlantic 2yo in training sale, Glengarry won his debut in August of his 2yo season and followed that up with a 12 3/4 length gate-to-wire win in the Iowa Cradle Stakes, brining his record to 2-for-2. Glengarry followed tear success up with a win in the Bowman Mill Stakes at Keeneland before rounding out his year with a strong 2nd place finish in the Springboard Mile at Remington Park.

At three, Glengarry took the Lafayette Stakes at Keeneland by 3 1/2 lengths, defeating MGSW Booth, in addition to SW/G3P Who Dey and Sis Doncho and Baytown Chatterbox.

At Four, Glengarry returned to Prairie Meadows where he took the Ed Skinner Stakes and followed that up with a win in the Iowa Sprint.