MLB: 5 Most Recent Chicago Cubs’ Playoff Appearances

Jonathan Daniel/Getty Images

What do Chicago Cubs greats Ernie Banks, Ron Santo, Ryne Sandberg and Sammy Sosa have in common? Other than their countless all-star appearances, historical statistics and numerous accolades, the quartet of former superstars never won a World Series with the north siders. In fact, they never even got the chance.

The Cubs, despite being a storied franchise in America’s National Pastime, have almost unfathomably not reached a World Series since 1945. Banks, Santo and Sandberg are each enshrined in the National Baseball Hall of Fame and the only thing keeping Sosa out are the performance-enhancing drugs allegations and such. Yet the group is just four of hundreds, if not thousands of players to sport the blue and white since their last championship in 1908.

Now, the Cubs 2015 fate is far from sealed. They still have to battle through the next few weeks to make it into the playoffs. Even if they are one of the final five National League squads standing, they will almost certainly have to take part in the do-or-die, one-game wild card playoff match, possibly on the road in Pittsburgh.

With the Cubbies faithful readying for an answer to the ever-present “Is this the year?” question this fall, let’s take a look at the team’s five most recent playoff appearances.

1. 1989 (Lost in NLCS 4-1)

CHICAGO - SEPTEMBER: Mark Grace #17 of the Chicago Cubs pops the ball up during a September 1989 game at Wrigley Field in Chicago, Illinois.
Jonathan Daniel/Getty Images

After not making the playoffs between 1945 and 1984, the Cubs finally broke through that season and made it to the National League Championship Series. They fell to the San Diego Padres in six games and did not make the postseason again until 1989.

Five years before moving to the NL Central, the Cubs earned first place in the six-team NL East with a record of 93-69 that season. With second-year manager Don Zimmer at the helm and Sandberg leading the offense, Chicago advanced to the NLCS again, this time to square off against the San Francisco Giants. With a nearly identical 92-70 regular season record, the Giants easily dispatched the Cubs.

Despite the home field advantage and throwing hall-of-famer Greg Maddux in game one, the Giants blew out the Cubs 11-3. Propelled by a six-run first inning in game two, the north siders took game two at home by a score of 9-5. Games three through five at Candlestick Park were decided by a total of four runs, but the Giants earned the win in each and closed the series in game five. Will Clark went 13-for-20 with a pair of home runs to earn series MVP honors. The Cubs pitching struggled to the tune of a 5.57 earned run average in the five games. The Giants ended up being swept in the World Series by the Oakland Athletics.

2. 1998 (Lost in NLDS 3-0)

Jonathan Daniel/Getty Images

The 1990’s were a mostly rough decade for Cubs fans; although to be fair, most decades have been since World War II. The team’s lone playoff appearance was in 1998, a year that featured plenty of regular season history as well.

The MLB summer of 1998 is well-known for featuring the great home run chase between Sosa, Mark McGwire and for a while, Ken Griffey Jr. While McGwire won the home run title and set the new regular season record for long balls with 70, it was Sosa who led his team to the playoffs. In May of that season, phenom pitcher Kerry Wood punched out a record-tying 20 Houston Astros batters as well.

Unfortunately for Sosa, Wood and company, they ran into the National League-best Atlanta Braves (106-56) in the division series. John Smoltz was lights out in a 7-1 shellacking of the Cubs in game one and a blown save in game two ended in an extra-inning, 2-1 heartbreaking defeat in the following contest. To add insult to injury, old friend Maddux nailed down the series sweep in Chicago in game three. The Cubs hitters posted a pitiful .181 batting average and scored just four runs in the trio of games.

3. 2003 (Lost in NLCS 4-3)

(JOHN ZICH/AFP/Getty Images)

Oh boy, this one hurt. After a relatively underwhelming division capture at 88-74 in 2003, the Cubs entered October baseball with a stacked, youthful pitching rotation led by Wood and Mark Prior. They also featured plenty of solid veteran bats including Sosa, Moises Alou and Kenny Lofton.

This really seemed like the year for this team as they knocked off the heavily-favored Braves in five games in the NLDS. After splitting the first two games of the NLCS at home against the Florida Marlins and taking games three and four on the road, it seemed like destiny for a return trip to the World Series. Despite being shutout in game five, the Cubs still just had to win one of the final two games, both of which would be played at the friendly confines of Wrigley Field.

With an three-run eighth inning lead and a mere five outs from a pennant, up stepped Luis Castillo. With the count 3-2, well, you know the rest…

Alou’s tirade was a perfect symbol of what was soon to transpire. The team’s eighth-inning implosion put game six to bed and the Marlins advanced to the World Series with a 9-6 victory in game seven.

4. 2007 (Lost in NLDS 3-0)

Dilip Vishwanat/Getty Images

Like in 1998, the Cubs barely had a chance to get their feet wet in the 2007 playoffs. After capturing the division crown at 85-77, Chicago was tasked with facing the Arizona Diamondbacks one of the two NLDS.

A pitcher’s duel between Carlos Zambrano and Brandon Webb ended in a D-Backs 3-1 win at Chase Field. in the first match. Game two featured much more offense, but the Cubs fell ultimately fell 8-4, shifting the series east with the season on the line.

A trio of Arizona home runs by Eric Byrnes, Stephen Drew and Chris Young in game three catapulted the NL West champions to a series-clinching, 5-1 win.

5. 2008 (Lost in NLDS 3-0)

LOS ANGELES, CA - OCTOBER 04: Manager Lou Piniella of the Chicago Cubs talks with manager Joe Torre of the Los Angeles Dodgers before Game Three of the NLDS during the 2008 MLB playoffs on October 4, 2008 at Dodger Stadium in Los Angeles, California. The Dodgers defeated the Cubs 3-1 to advance to the NLCS.
Jeff Gross/Getty Images

2008 seemed like another great chance for the Cubs to get that elusive title. They finished the regular season first in the NL Central with an outstanding 97-64 mark. Legendary manager Lou Piniella was in his second year in the role and still had the bitter taste of the 2007 sweep in his mouth.

Despite a solid front-end of the rotation with Ryan Dempster, Rich Harden and Carlos Zambrano, each one faltered in the division series. They allowed 12 runs combined in their starts and the 84-win Los Angeles Dodgers handed the Cubs another early playoff exit.

L.A. outscored Chicago 17-5 in the opening two games at Wrigley Field. A strong outing from Hiroki Kuroda in game three resulted in a 3-1, NLDS-closing win.

All data courtesy of