September 29
Won second game in Philadelphia when he beat his brother Mike Maddux. Both were rookies, it was the first time two brothers had faced each other as rookies.

Season Highlights
Spent most of the year in the Cubs farm system at Iowa. Finished the season with a 2-4 record and a 5.52 ERA.
Named to Baseball America’s 1986 Class AAA All-Star team.

August
Twice optioned down to AAA Iowa.

September 4
Promoted to the majors. Been there since.

September 24
Against Philadelphia he tossed his first 10-strikeout game.

Season Highlights
Began the season at Class AAA Iowa before being promoted to the Cubs’ starting rotation. Finished the year 6-14 with a 5.61 ERA losing his last six decisions. This would be the last time Greg would finish a season with a losing record.

June
Named Pitcher of the Month for June after going 5-0 with a 2.22 ERA

Season Highlights
Was 15-3 going into the All-Star break, including a nine-game win streak from May 22 to July 10.
At 22, became the youngest Cub named to the All-Star team.
Finished the season 18-8 with a 3.18 ERA.

Season Highlights
Compiled a 15-15 record and a 3.46 ERA.
Opened the season by winning four of his first five starts, then lost eight in a row from May 11 to July 14. Followed that losing streak by winning his next five starts.
Won his first Gold Glove award. Becoming the first Cub pitcher to ever accomplish this feat.
Started a league-high 35 games and completed eight.
His 39 putouts for the year tie the NL season mark of Vic Willis.

Season Highlights
Led the National League with 37 starts and 263 innings pitched. The 37 starts were the most by a Cub since Rick Reuschel had 38 and Dennis Lamp had 37 in 1980.
Finished 15-11 with an ERA of 3.35.
Posted a 2.92 ERA in his last 18 starts.
Struck out 198 batters, second most in the National League, and walked only sixty-six.
Won his second Gold Glove award

July 5
Maddux defeats the Atlanta Braves handily. The starter for the Braves is John Smoltz.

July 16
In Pittsburgh, Greg announces he has broken off talks with the Cubs management and would become a free agent after the season. Maddux comments “I’ve given them two opportunities to sign me. I really think it should be taken care of.” Despite showing the frustrations of contract talks Maddux goes out the next day and beats the first place Pirates.

July 27
In his first start at Wrigley Field since his announcement that he is leaving, Greg goes out and defeats the Pirates and Doug Drebeck. Maddux is given a standing ovation in the eight inning.

August 16
Allowing only four hits, Greg picks up his 15th win of the season. This becomes the fifth year in a row Maddux has won 15 games.

September 30
Greg becomes the Cubs first 20 game winner in 15 years when he beats the Pirates 6-0.

December 9
Signed by the Atlanta Braves as a free agent. The five year deal is worth 28 million. The Cubs offered 28.5 million during the season. The news is a stun to the Yankees who offered Maddux an additional 6 million. The signing brings an end to the days of Charlie Leibrant as Leibrant is traded to the Rangers.

Season Highlights
Won his first Cy Young Award. Selected to his second All-Star game. Won his third Gold Glove award.
In his seventh and last season with the Cubs, went 20-11 with a 2.18 ERA.
After the All-Star break, he went 10-3 and maintained a 1.93 ERA.
Became the first Cub since 1977 to win 20 games.
His 20 wins tied Tom Glavine for the NL lead.
Posted a 12-4 record and a 1.91 ERA at Wrigley Field.
In his 11 losses, the Cubs scored just eight runs and were shut out seven times.
Led the league with 268 innings pitched, allowing just 7 homeruns.