Early yearsLomita, California. He broke into the majors with the Montreal Expos in 1999, pitching in only nine games that year before being traded to the New York Yankees as part of a trade involving Hideki Irabu. Lilly played for more than two years for the Yankees before being dealt to the Oakland Athletics in a three team deal that included pitchers Jeff Weaver heading to New York and Jeremy Bonderman going to the Detroit Tigers. Lilly was in the starting rotation for Oakland, and pitched in the American League Division Series in both 2002 and 2003.
2004 seasonBobby Kielty. He made the American League All-Star team in 2004 as the Jays' lone representative that year.
The highlight of his career as a Blue Jay was a start on August 23, 2004 against the Boston Red Sox. He pitched a complete-game shutout and struck out 13 batters in a three-hit 3–0 victory.
2006 seasonLilly was 15–13 with a 4.31 ERA and 160 strikeouts in 2006, exceeding his previous career-high for wins (12). He also equaled a career high for starts (32) and nearly matched his career highs in strikeouts and innings pitched. This season, he ranked first among the Jays' pitching staff in strikeouts and second only to Roy Halladay in wins (Halladay had a 16–5 record before a recurring elbow injury ended his season in late September).
On August 21, 2006, in a game against the Oakland Athletics, Lilly was surrendering an early 8-0 lead in the 3rd inning when manager John Gibbons took him out of the game. With the score 8-5 and runners on 1st and 3rd, Lilly refused to give him the ball. Eventually, he reluctantly left the mound and later feuded with Gibbons in the locker room, though Gibbons maintained no punches were thrown.
Barry Zito, Jason Schmidt and Jeff Suppan, was one of the most sought-after free agent pitchers, partially due to the thin market for starting pitching. On the morning of December 6, 2006, he informed the Blue Jays that he would not be returning to the club, thus rejecting a four year, $40 million deal. He cited a "change in scenery" as his reasoning. Later on that day, Lilly agreed to an identical four year, $40 million deal with the Chicago Cubs, officially ending his tenure with the Blue Jays.
In his first start for the Cubs, Lilly defeated the Cincinnati Reds in a strong outing, taking a no hitter into the fifth inning, and only yielding one earned run over seven innings. Lilly then was the starting pitcher for the Cubs home opening game at Wrigley Field on April 9, 2007. Lilly gave up three runs in six innings, but did not factor into the decision. Lilly pitched well in April, lasting at least six innings in each of his five starts while never giving up more than three runs in a game posting a 2.18 ERA.Lilly was prominent in a contentious series in Atlanta between the Cubs and the Atlanta Braves. In game one of the series, Alfonso Soriano hit three home runs in his first three at-bats as part of a Cubs 9-1 victory. In the next game, Tim Hudson hit Soriano with a first-pitch fastball triggering home-plate umpire Tim Tschida to issue warnings to both teams. On the final game of the series, Lilly hit Edgar Rentería in the first inning, and was promptly thrown out of the ballgame by Jim Wolf. Lilly was not suspended for his actions in the game.
2009 World Baseball ClassicWorld Baseball Classic.
In the first game he faced Venezuela but was pulled after 36 pitches. Manager Davey Johnson wanted to get work for starter Jeremy Guthrie and as many relievers as possible. Lilly left with the United States trailing 1-0, thanks to the homer he served up to his former Cubs batterymate, Henry Blanco. His second start was against Puerto Rico, a game that Team USA would win with a David Wright two-run single in the bottom of the ninth. For his part Lilly gave up two home runs, the only two hits he gave up in his 3 1/3 innings.
2010 seasonOn June 13, 2010, Lilly took a no-hitter into the 9th against the Chicago White Sox. In the ninth, he gave up a lead off single to Juan Pierre, then was lifted for relief pitcher Carlos Mármol, who got the save, getting out of a bases loaded jam, for a 1-0 Cub victory. This was the longest outing that Lilly held a team hitless. The no-hitter would have been the first pitched at Wrigley Field since Milt Pappas in 1972.
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