Cuellar's best years were spent with the Orioles, helping them capture five American League East Division titles, three consecutive American League pennants and the 1970 World Series Championship. He shared the AL Cy Young Award in 1969 and won 20-or-more games in a season four times from 1969 to 1974. He was a part of the last starting rotation to feature four pitchers with at least twenty victories each in one season.

This 8x10 photo has been signed in black by Cuellar and inscribed, "1970 W.S. Champs." This item includes an A.P.E. hologram.