1999 Game Log
| Date | Location | Score | Winner |
| June Series — Wrigley Field |
| June 11 | Wrigley Field | Sox 5–3 | White Sox W: Parque L: Lieber. Norton and Blauser HR, in this rain shortened 5.5 inning game that lasted 1:38 hours. |
| June 12 | Wrigley Field | Sox 8–2 | White Sox W: Sirotka L: Trachsel. Thomas and Johnson HR. Sox get 18 hits. |
| June 13 | Wrigley Field | Sox 6–4 | White Sox W: Simas L: Aguilera SV: Foulke. Sox sweep Wrigley. |
| July Series — New Comiskey Park |
| July 9 | New Comiskey Park | Sox 3–2 | White Sox W: Howry L: Adams. Close one — Sox walk it off in the 9th. |
| July 10 | New Comiskey Park | Cubs 10–2 | Cubs W: Lieber L: Navarro. Hill, Hernandez, Konerko all HR. Cubs rout. |
| July 11 | New Comiskey Park | Cubs 6–3 | Cubs W: Trachsel L: Baldwin SV: Adams. Houston, Hill, Singleton HR. |
1999 Series Notes
The 1999 Crosstown Classic split into two distinct stories. Act One: the Sox come to Wrigley in June and absolutely handle the Cubs, sweeping all three games. Frank Thomas, Magglio Ordonez, and a young Carlos Lee gave the Cubs fits. Mike Sirotka was especially dominant in Game 2, limiting the Cubs to 2 runs on 8 hits while the Sox pounded out 18 hits of their own.
Act Two: the Cubs come to New Comiskey in July looking for revenge. The Sox took Game 4 in a close 3-2 win. Then the Cubs answered with two convincing victories to finish strong. Game 5 was a 10-2 rout — Glenallen Hill and Jose Hernandez homered, and a young Paul Konerko also went deep for the Sox in a losing cause. Konerko was just 23 years old and was still establishing himself. Nobody knew yet what that kid would become against the Cubs over the next decade.
Sox win the series 4-2. After three years of the Crosstown Classic, the all-time record stood at Cubs 6, Sox 6 — dead even heading into 2000.
Box Scores & Lineups — June Series (Wrigley Field)
Game 1 — Sox Win — June 11, 1999 — Wrigley Field — Day Game
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago White Sox | 1 | 0 | 4 | 0 | 0 | 0 | - | - | - | 5 | 11 | 1 |
| Chicago Cubs | 0 | 0 | 1 | 0 | 2 | - | - | - | - | 3 | 5 | 2 |
Chicago White Sox
1. Ray Durham (2B)
2. Mike Caruso (SS)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Chris Singleton (CF)
7. Greg Norton (3B)
8. Brook Fordyce (C)
9. Jim Parque (P)
Mgr: Jerry Manuel
Chicago Cubs
1. Jeff Blauser (3B)
2. Manny Alexander (2B)
3. Mark Grace (1B)
4. Sammy Sosa (CF)
5. Glenallen Hill (RF)
6. Henry Rodriguez (LF)
7. Benito Santiago (C)
8. Jose Hernandez (SS)
9. Jon Lieber (P)
Mgr: Jim Riggleman
Game 2 — Sox Win — June 12, 1999 — Wrigley Field — Day Game
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago White Sox | 1 | 0 | 1 | 3 | 0 | 3 | 0 | 0 | 0 | 8 | 18 | 3 |
| Chicago Cubs | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 2 | 2 | 8 | 0 |
Chicago White Sox
1. Ray Durham (2B)
2. Mike Caruso (SS)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Chris Singleton (CF)
7. Greg Norton (3B)
8. Mark Johnson (C)
9. Mike Sirotka (P)
Mgr: Jerry Manuel
Chicago Cubs
1. Jeff Blauser (SS)
2. Jose Hernandez (CF)
3. Mark Grace (1B)
4. Sammy Sosa (RF)
5. Glenallen Hill (LF)
6. Gary Gaetti (3B)
7. Benito Santiago (C)
8. Mickey Morandini (2B)
9. Steve Trachsel (P)
Mgr: Jim Riggleman
Game 3 — Sox Win — June 13, 1999 — Wrigley Field — Day Game
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago White Sox | 0 | 0 | 1 | 1 | 0 | 0 | 2 | 2 | 0 | 6 | 12 | 0 |
| Chicago Cubs | 0 | 2 | 0 | 1 | 0 | 1 | 0 | 0 | 0 | 4 | 7 | 1 |
Chicago White Sox
1. Ray Durham (2B)
2. Mike Caruso (SS)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Chris Singleton (CF)
7. Greg Norton (3B)
8. Brook Fordyce (C)
9. Jaime Navarro (P)
Mgr: Jerry Manuel
Chicago Cubs
1. Curtis Goodwin (CF)
2. Mickey Morandini (2B)
3. Sammy Sosa (RF)
4. Mark Grace (1B)
5. Henry Rodriguez (LF)
6. Tyler Houston (C)
7. Gary Gaetti (3B)
8. Jose Hernandez (SS)
9. Kevin Tapani (P)
Mgr: Jim Riggleman
Box Scores & Lineups — July Series (New Comiskey Park)
Game 4 — Sox Win — July 9, 1999 — New Comiskey Park — Night
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago Cubs | 0 | 0 | 0 | 0 | 0 | 1 | 1 | 0 | 0 | 2 | 9 | 1 |
| Chicago White Sox | 0 | 1 | 0 | 0 | 1 | 0 | 0 | 0 | 1 | 3 | 9 | 0 |
Chicago Cubs
1. Jeff Blauser (2B)
2. Manny Alexander (SS)
3. Mark Grace (1B)
4. Sammy Sosa (RF)
5. Glenallen Hill (DH)
6. Jose Hernandez (LF)
7. Benito Santiago (C)
8. Gary Gaetti (3B)
9. Curtis Goodwin (CF)
Mgr: Jim Riggleman
Chicago White Sox
1. Ray Durham (2B)
2. Chris Singleton (CF)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Paul Konerko (DH)
7. Greg Norton (3B)
8. Mark Johnson (C)
9. Mike Caruso (SS)
Mgr: Jerry Manuel
Game 5 — Cubs Win — July 10, 1999 — New Comiskey Park — Day Game
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago Cubs | 0 | 0 | 3 | 1 | 0 | 2 | 0 | 0 | 4 | 10 | 12 | 1 |
| Chicago White Sox | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 1 | 1 | 2 | 8 | 3 |
Chicago Cubs
1. Mickey Morandini (2B)
2. Tyler Houston (3B)
3. Sammy Sosa (RF)
4. Mark Grace (1B)
5. Henry Rodriguez (DH)
6. Glenallen Hill (LF)
7. Jeff Reed (C)
8. Jose Hernandez (SS)
9. Curtis Goodwin (CF)
Mgr: Jim Riggleman
Chicago White Sox
1. Ray Durham (2B)
2. Chris Singleton (CF)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Paul Konerko (DH)
7. Greg Norton (3B)
8. Brook Fordyce (C)
9. Mike Caruso (SS)
Mgr: Jerry Manuel
Game 6 — Cubs Win — July 11, 1999 — New Comiskey Park — Night
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | R | H | E |
| Chicago Cubs | 0 | 2 | 3 | 0 | 0 | 0 | 1 | 0 | 0 | 6 | 7 | 0 |
| Chicago White Sox | 0 | 0 | 2 | 0 | 0 | 0 | 0 | 1 | 0 | 3 | 6 | 0 |
Chicago Cubs
1. Mickey Morandini (2B)
2. Tyler Houston (3B)
3. Sammy Sosa (RF)
4. Mark Grace (1B)
5. Henry Rodriguez (DH)
6. Glenallen Hill (LF)
7. Jeff Reed (C)
8. Jose Hernandez (SS)
9. Curtis Goodwin (CF)
Mgr: Jim Riggleman
Chicago White Sox
1. Ray Durham (2B)
2. Chris Singleton (CF)
3. Frank Thomas (1B)
4. Magglio Ordonez (RF)
5. Carlos Lee (LF)
6. Paul Konerko (DH)
7. Greg Norton (3B)
8. Mark Johnson (C)
9. Craig Wilson (SS)
Mgr: Jerry Manuel