[2] Timberlake made his debut on June 5 in a maiden special weight event over 5+1⁄2 furlongs at Ellis Park.
[4] On his next start Ellis Park over seven furlongs Timberlake made amends, leading all the way to win by over nine lengths over West Saratoga in 1:23.38.
[5] In the Grade 1 Hopeful Stakes at Saratoga Race Course, Timberlake started at 11/5 odds and hit the front in the stretch run but was beaten by the longshot Nutella Fella by a length-and-a-half in a time of 1:24.41.
[7] After the start jockey Florent Geroux had moved Timberlake up to third in the field of eight 2-year-olds, then swung about seven paths wide to launch a bid for the lead.
Timberlake grabbed the lead before the eighth pole and pulled away in the final sixteenth winning by 4+1⁄4 lengths in 1:35.90 on a sloppy track.
On February 24, 2024, Timberlake began his three-year-old in the Grade II Rebel Stakes at Oaklawn Park.