Dalrymple backed up Elrod Hendricks and Andy Etchebarren, helping the Orioles win the American League championship, before losing to the in the 1969 World Series. He made two pinch-hitting appearances in the '69 World Series, getting 2 singles in 2 at-bats in the third and fourth games. He suffered a broken ankle during the 1970 season and hadn't recovered in time to be activated for the Orioles' victory in the 1970 World Series. He played sparingly in 1971 during which the Orioles again won the American League championship, before losing to the Pittsburgh Pirates in the 1971 World Series. Dalrymple didn't play in any of the Orioles' postseason games that year. When the Orioles announced that they would assign him to their Triple-A team, the Rochester Red Wings, Dalrymple decided to retire from baseball.