1998, Timlin signed a four-year, $16 million contract with the Baltimore Orioles. During the 1999 season, he appeared in 62 games for the Orioles, with a record of 3–9, 27 saves and a 3.57 ERA. For the 2000 season, he was with the Orioles through late July, appearing in 37 games, with a record of 2–3, 11 saves and a 4.89 ERA. On July 29, 2000, Timlin was traded (along with cash) to the St. Louis Cardinals in exchange for Chris Richard and minor league player Mark Nussbeck. In two seasons with Baltimore, Timlin appeared in a total of 99 games, compiling a record of 5–12, with 38 saves and a 4.04 ERA, while striking out 76 and walking 38 in 98 innings pitched. St. Louis Cardinals Timlin made his first appearance with the Cardinals (and in the National League) on July 30, 2000, pitching one inning in relief against the New York Mets. He made 25 total appearances with the Cardinals during the regular season; he had a 3–1 record, with one save and a 3.34 ERA. He appeared in two games of the National League Division Series (NLDS) against the Atlanta Braves, and in three games of the National League Championship Series (NLCS) against the Mets. He took the loss in Game 2 of the NLCS, giving up an unearned run while pitching the ninth inning. For the 2001 season, Timlin appeared in 67 games with St. Louis; he had a 4–5 record, three saves, and a 4.09 ERA. He had his first major league at bat on October 6 against the Houston Astros, grounding out in the fifth inning. He made one appearance in the postseason, pitching scoreless innings against the Arizona Diamondbacks in the NLDS. During the 2002 season, he was with the Cardinals through late July, appearing in 42 games, with a record of 1–3 and a 2.51 ERA. On April 19, he made his first start since his rookie season, taking the loss against the Milwaukee Brewers; he pitched innings, giving up four runs (all earned) while striking out three batters and walking one. On July 29, 2002, Timlin, Plácido Polanco, and Bud Smith were traded to the Philadelphia Phillies in exchange for Doug Nickle, Scott Rolen, and cash. In his three seasons with St. Louis, Timlin appeared in 134 games, compiling a record of 8–9, with four saves and a 3.36 ERA. In