Injuries hampered Fryman in 1999. He rebounded to have his best season in 2000. He established career highs in batting average (.321), slugging percentage (.516), on-base percentage (.392), hits (184), doubles, and RBIs (106). Additionally, he also only made eight errors in the field and had a 60-game errorless streak, on his way to winning a Gold Glove Award. His teammates rewarded his efforts with the Gordon Cobbledick Golden Tomahawk Award, and the Cleveland Baseball Writers' Association named him their Man of the Year.