Table of Contents

    Playoff win droughts are some of the most painful for fans to endure. Not winning a championship is tough, and missing the playoffs for years on end is futile, but the hope a playoff berth provides, only for it to be immediately quashed with no further celebration, is a brutal experience.

    The regular season is nice, but the playoffs make legacies. Every year, many teams qualify for their respective playoffs, but only half of them advance beyond the first round. For some sides, it’s been a while since achieving that second stage. These are the pro sports teams suffering from the longest playoff win droughts.

    Longest Playoff Win Droughts in Pro Sports

    T-9: Washington Commanders (NFL)

    Last Playoff Win: 2005 (17-season drought)

    At 10-6, Washington earned the No. 6 seed in the NFC in 2005. In the Wild Card Round, the team traveled south to take on the NFC South-champion Buccaneers. Despite 120 total yards of offense, the visitors won the day. Sean Taylor returned a fumble for a touchdown in the first quarter, LaVar Arrington and Marcus Washington had an interception each, and the defense stopped Tampa Bay on two fourth downs to will Washington to a 17-10 victory.

    This marked the last time this franchise advanced in the playoffs. Washington lost, 20-10, in Seattle the next week and has failed to win a game in any of its three postseason appearances since. Most recently, the Washington Football Team bowed out to the Bucs in 2020, 31-23.

    T-9: Chicago White Sox (MLB)

    Last Playoff Win: 2005 (17-season drought)

    On Oct. 26, 2005, the White Sox completed a World Series sweep of the Astros, 1-0, to win their first title since 1917. It ended one of the longest championship droughts in North American sports history and it built on the magical mystique of Ozzie Guillen. The White Sox lost just one game in that entire postseason.

    AP Photo/Amy Sancetta

    That was the last time the franchise won a playoff series. Chicago has mostly missed the playoffs in the 17 years following its World Series but failed to advance a round in any of its three qualifications. In 2021, the White Sox took on the Astros in the ALDS but couldn’t get through, 3-1, allowing the losing streak to live.

    T-9: Toronto Maple Leafs (NHL)

    Last Playoff Win: 2004 (17-season drought)

    The Leafs are the not-so-proud owners of the longest playoff win drought in the NHL.

    As the East’s No. 4 seed, Toronto took on the Senators in the Conference Quarterfinals. The teams traded wins back and forth the entire series, which ultimately played out in the higher seed’s favor. In that series, Joe Nieuwendyk scored five goals and Ed Belfour recorded a .954 save percentage.

    The Leafs luck ran out in the Conference Semifinals against the Flyers, 4-2. It’s been nothing but pain and suffering for Toronto in the playoffs in the years since. In 2013, the Maple Leafs blew a 4-1 lead in the third period of Game 7 against the Bruins and lost in overtime. Toronto has participated in every postseason since 2017 and lost in the first round every time. For the last five seasons, the Leafs have pushed all of their initial series to the brink, only to flop in Game 7 (or effective Game 7s – thanks, 2020).

    Currently, Toronto is second in the Atlantic and 16 points above fourth place. The Leafs will likely get another shot at redemption this spring.

    T-6: Minnesota Timberwolves (NBA)

    Last Playoff Win: 2004 (18-season drought)

    The Timberwolves had the second-best record in the 2003-04 NBA and served as the West’s No. 1 seed in the 2004 postseason. First, Minnesota dispatched the Nuggets, 4-1. Then, the Kings took the T-Wolves to seven, but the top seed narrowly got it done in Game 7, 83-80, to reach the Western Conference Finals. That’s where the dream of the franchise’s first NBA title died – Kobe Bryant, Shaquille O’Neal, and the Lakers outdid Kevin Garnett, Latrell Sprewell, and the Timberwolves, 4-2.

    AP Photo/Ann Heisenfelt

    Minnesota didn’t reach the postseason again, let alone win a series, for another 14 years. The Timberwolves have played in the playoffs twice since their last advancement and lost in the first round both times, most recently in 2022 to the Grizzlies, 4-2.

    T-6: Charlotte Hornets (NBA)

    Last Playoff Win: Never (18-season drought)

    So, this is a weird one. In 2002, the Charlotte Hornets became the New Orleans Hornets. In their final season in Charlotte, those Hornets won in the first round before bowing out. But those Hornets aren’t these Hornets – the NBA awarded Charlotte an expansion franchise in 2004 and named them the Bobcats, then the old Hornets switched to the Pelicans years later. The Bobcats eventually rebranded to these Hornets, and these Hornets have never won a playoff series.

    This franchise has been in the playoffs three times. Its latest appearance was in 2016, and the Hornets came so close to getting over the hump. They were up 3-2 on the Heat but couldn’t close out the series in Game 6. In Game 7, Miami crushed Charlotte, 106-73, and the Hornets haven’t been back to the postseason.

    T-6: Sacramento Kings (NBA)

    Last Playoff Win: 2004 (18-season drought)

    The Kings were the No. 4 seed in the West in the 2004 NBA Playoffs, their sixth-straight appearance in the postseason. In the first round, they faced off with Dirk Nowitzki and the Mavericks. Though three of the victories were played within four points, Sacramento made relatively quick work of Dallas, 4-1, behind Mike Bibby’s 23.6 points and 2.4 steals per game. In the second round, the Kings were tasked with the top-seeded Timberwolves. Sacramento pushed the series all the way to seven but suffered elimination by just three points in the deciding contest.

    The team made the playoffs in each of the next two seasons but failed to advance in either attempt. Sacramento hasn’t escaped the regular season since 2006, the longest active playoff drought across the NBA, NFL, MLB, and NHL. Currently, the Kings are on pace to snap that streak. If they do, it would be efficient to put this one to bed, too.

    T-4: Las Vegas Raiders (NFL)

    Last Playoff Win: 2002 (20-season drought)

    Twenty years ago, Rich Gannon threw for 286 yards and three touchdowns in the AFC Championship Game to lead the Raiders to their first Super Bowl since 1983. The AFC’s top seed took down Steve McNair and the Titans, 41-24, to set up a date with the Buccaneers in the final contest.

    That game did not go as well as the first two playoff ones did for Oakland. Michael Pittman ran for 124 yards against the Raiders and the Bucs scored three defensive touchdowns to rout their way to their inaugural NFL championship, 48-21.

    It’s been only playoff Ls for this franchise in the two succeeding decades. They’ve been back to the postseason just twice in the last 20 years – 2016 and 2021 – and couldn’t get to the Divisional Round in either try. In their 2021 Wild Card game, the Raiders outgained the Bengals but committed two costly turnovers that couldn’t be overcome. Cincinnati went on, 26-19, and Las Vegas continued its search for that elusive postseason W.

    T-4: Minnesota Twins (MLB)

    Last Playoff Win: 2002 (20-season drought)

    With 94 wins, the Twins carried the flag for the AL Central into the 2002 MLB Playoffs. It was their first time back in the postseason after missing it every campaign following their 1991 World Series crown. Minnesota met the 103-win Athletics in the ALDS and traded blows until the end, edging out Oakland in Game 5, 5-4, to win the series. The ALCS versus the Angels didn’t go as well, and the Twins were sent home in five games.

    AP Photo/Tony Gutierrez

    The team made the playoffs in five of the next eight years but didn’t win a series on any try. The Twins have played in the postseason three times since 2017 and have still been unable to end this horror. The franchise hasn’t even won a single playoff game since 2004 despite multiple ALDS appearances. It’s been a tough couple of decades for Twins fans.

    3: Miami Dolphins (NFL)

    Last Playoff Win: 2000 (22-season drought)

    It was Miami’s fourth-straight playoff appearance when the No. 3-seeded AFC East champs matched up with the Colts in the 2000 NFL Wild Card Round. The Dolphins turned the ball over three times in the first half but overcame those mistakes, in part thanks to Lamar Smith’s 209 rushing yards on 40 carries, the most in a single playoff game in NFL history. Jay Fielder drove Miami down the field and threw a touchdown to Jed Weaver in the final minute of regulation to force overtime, then Mike Vanderjagt’s miss on the Colts’ first overtime possession opened the door for the Dolphins to do it again. They did, and Smith scored the game-winning TD.

    Hopefully, that thriller has lived long in the memory of Dolphins fans because they’ve had nothing since. The Raiders rocked Miami in the next game, 27-0, which started a five-game playoff losing streak that the Dolphins extended this season. In 2022, Miami returned to the postseason for the first time since 2016 and had a second-half lead over the Bills. But the Dolphins gave that away by the middle of the third quarter, and Buffalo defeated its division rival, 34-31. It’s now been 22 years since South Florida celebrated a playoff win, one of the longest droughts in sports.

    2: Cincinnati Reds (MLB)

    Last Playoff Win: 1995 (27-season drought)

    Cincinnati topped the 1995 NL Central for its first return to the playoffs since winning the 1990 World Series. In the NLDS, the Reds went up against the Dodgers and discarded their former division rival with haste. Cincinnati swept LA, 3-0, including a 10-1 hammering via three home runs and eight David Wells strikeouts to seal the deal in Game 3. In the NLCS, the Braves gave the Reds a taste of their own medicine. It took four games for Atlanta to eliminate Cincinnati and end its hope of another NL pennant.

    In the 27 seasons since the Reds defeated the Dodgers, they’ve made four postseason appearances and failed to advance in all of them. The closest the team came was in 2012, blowing a 2-0 series lead to the Giants and falling in Game 5, 6-4. Most recently, Cincinnati played in the 2020 NLWC but lost to the Braves twice in a row to meet its demise.

    Cincinnati is responsible for the longest-running playoff win drought in the MLB by seven years. The once-mighty Reds have had a difficult three decades and have quite the monkey to get off their backs.

    1: Detroit Lions (NFL)

    Last Playoff Win: 1991 (31-season drought)

    America was still 10 months away from electing Bill Clinton to his first presidential term when the Lions last won a playoff game.

    A 12-4 regular season gave Detroit an NFC Central title – a division that hasn’t existed for 20 years – and the No. 2 seed in its conference. The Cowboys won their Wild Card game to get a date with the Lions in Detroit, and it did not go well for the traveling side. Erik Kramer threw for 341 yards and Dallas turned the ball over four times as Detroit pummeled the lower seed, 38-6. It was the franchise’s first playoff victory in the Super Bowl era.

    The Lions are still hunting for that second Super Bowl-era postseason triumph. After demolishing Dallas, Detroit took a beating of its own: 41-10 to Washington. In the 31 seasons since, the Lions have made the playoffs eight times but never left the field celebrating in any of those attempts. The last chance was in 2016 as the NFC’s No. 6 seed, which produced a 26-6 defeat in Seattle.

    AP Photo/Elaine Thompson, File

    There aren’t many nice things to say about the Lions. This franchise has to be considered one of the least successful in sports over the last 60 years. This streak is the fifth-longest of its kind in NFL history, and the Lions are just a few more failures away from matching and surpassing the 33-year winless postseason run they compiled from 1958 until 1991, which is tied for third on the all-time list.

    This team has provided its fans with little to enjoy for a very, very long time.


    What's On Tap: The Waste Management Phoenix Open


    Does Everyone Stink? A College Basketball Investigation

    NHL Power Ranking Playoff Pools for 2024

    NHL Pick'em


    NBA Playoff Pools for 2024

    NBA Pick'em


    NBA Playoff Pools for 2024

    NBA Pick'em


    NHL Playoff Pools for 2024

    NHL Pick'em


    NHL Playoff Pools for 2024

    NHL Pick'em


    NFL Playoff Bracket Pools for 2024

    NFL Pick'em


    Check Also