In 2000, Fingleson hit .348 for the Catskill Cougars, placing him fourth in the Eastern Division of the Northern League, as he played second base, third base, and shortstop. The Cougars were loaded with Australians as teammates, including Greg Jelks and Brendan Kingman. In the 2000–01 IBLA, he batted .314 to finish fourth in average and third in hits with 49; only A. J. Zapp, Travis Wilson, and Glenn Williams had better batting averages. He struck out in only nine of his 156 at bats, the lowest rate in the circuit. He again made the league All-Star team at designated hitter.