After the 1966-67 season, Barry became one of the first NBA players to jump to the American Basketball Association when he signed with the Oakland Oaks. In the ABA's first season, the Oaks were the only ABA team located in the same market as an NBA team (the Warriors). The Warriors went to court and prevented Barry from playing for the Oaks during the 1967-68 season. Barry instead worked on Oaks radio broadcasts during the ABA's first season.  During the 1968-69 season Barry suited up for the Oaks and averaged 34 points per game. He also led the ABA in free throw percentage for the season (a feat he repeated in the 1970-71 and 1971-72 seasons). However, on December 27, 1968, late in a game against the New York Nets, Barry and Kenny Wilburn collided and Barry tore ligaments in his knee. He tried to play again in January but only aggravated the injury and sat out the rest of the season, only appearing in 35 games as a result. Despite the injury Barry was named to the ABA All-Star team. The Oaks finished with a record of 60-18, winning the Western Division by 14 games over the second place New Orleans Buccaneers. In the 1969 ABA Playoffs the Oaks defeated the Denver Rockets in a seven-game series and then defeated New Orleans in the Western Division finals. In the finals the Oaks defeated the Indiana Pacers 4 games to 1 to win the 1969 ABA Championship.  The Oaks' on-court success had not translated into solid attendance. The team averaged 2,800 fans per game. Instead of remaining in Oakland for another season to see if the championship would draw fans, the team was sold by owner Pat Boone and relocated to Washington, D.C. for the 1969-70 season.

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