Cleveland Browns Top Gut-Wrenching Playoff Losses of All Time

Those fans above a certain age may remember when the Cleveland Browns ran roughshod over most other teams in the league. Browns fans born after 1964 don’t have these memories. However, they  hold many painful recollections of games gone wrong and of sure things evaporating right in front of their eyes.

John Greenleaf Whittier was spot-on when he wrote “of all sad words of tongue or pen, the saddest are these: “It might have been!” In Cleveland we have more than our fair share of it might have been, if only, and almost moments. So many, in fact, there is a montage a certain network plays whenever a Cleveland team loses in a playoff game. (Looking at you, ESPN)

Strength through adversity has been a mantra in Cleveland for decades. Here are some examples of this in action.

The 1968 NFL Championship Game against the Baltimore Colts

During the 1968 regular season, the Cleveland Browns were the only team to defeat the Colts. So, when it was time to decide which powerhouse would face the New York Jets in Super Bowl III, the Colts were locked and loaded. Their revenge came via a 34-0 beatdown. This was the closest the Browns would come to the Super Bowl for many years.

Red Right 88- 1980 AFC Divisional Playoff Against the Oakland Raiders

Cleveland’s old Municipal Stadium was more like a frozen tundra than a football field. The beloved Kardiac Kids kept pace with the Oakland Raiders but were down by two. With less than a minute to play and the ball on the 13-yard line, Browns coach Sam Rutigliano called for a pass rather than trying a game-winning field goal. The play “Red Slot Right, Halfback Stay, 88,” could have resulted in a winning touchdown. Instead, it was intercepted in the end zone, and the Raiders prevailed.

They died by it (Red Right 88)

The Drive – 1987 AFC Championship vs the Denver Broncos

Several years after Red Right 88 crushed the hearts of Browns fans, the team was in the hunt for a Super Bowl appearance. The Browns had a 20-13 lead. With the AFC Championship on the line and 5:32 on the clock, the Denver Broncos got the ball on the 2-yard line. The rest is a nightmarish comeback that haunts Cleveland to this day. Quarterback John Elway led his team 98 and scored, tying the game. In overtime, the Broncos kicked a game-winning field goal, and the rest is history.

‘The Drive’: Browns vs. Broncos 1986 AFC Championship Game highlights

 The Fumble- 1988 AFC Championship vs the Denver Broncos

The venue was Denver’s Mile High Stadium, and the Browns were prepared to avenge their AFC Championship loss from the previous season. Most fans believed that lightning could not strike twice. However, after a competitive game, the Browns were down 38-31 with just over a minute left. Browns’ running back, Ernest Byner, was on his way to the end zone for a game-tying touchdown when he fumbled the ball on the 2-yard line. Denver recovered and went on to win the game.

“The Fumble” (Browns vs. Broncos, 1987 AFC Championship) | NFL Vault Highlights

1994 AFC Divisional Round vs the Pittsburgh Steelers

Odd as it sounds, this was the first playoff game between these two bitter rivals. The Browns’ head coach, Bill Belichick, and his squad were overrun by the Steelers’ defense, scoring only 9 points in the 29-9 debacle.

FIRST Ever Pittsburgh-Cleveland Playoff Matchup! (Browns vs. Steelers 1994 AFC Divisional Round)

2002 Wild Card vs the Pittsburgh Steelers

The first playoff meeting between the new era Cleveland Browns and rival Pittsburgh Steelers was an exciting contest. Until it wasn’t. By the 4th quarter, Cleveland had squandered a 33-21 lead. The Steelers scored 15 unanswered points and advanced in the playoffs, 36-33.

An Iron City Classic Comeback! (Browns vs. Steelers, 2002 AFC Wild Card) | NFL Vault Highlights

2020 Divisional Playoff vs the Kansas City Chiefs

The Browns took on the defending Super Bowl Champion Kansas City Chiefs, fresh off the team’s first playoff win since 1994. The Browns fought but remained behind the Chiefs, although they eventually closed the gap to just 5 points. The result was a Cleveland loss 22-17. However, the game had controversy.

Many in Cleveland, and across the sports world, believe the most pivotal play of the game was when the officials failed to call a helmet-to-helmet hit Chiefs’ safety Daniel Sorensen delivered to Browns’ receiver Rashard Higgins. The illegal hit resulted in a fumble into the end zone, which led to the enforcement of an obscure rule that declared the play a touchback.

If the officials had spent more time calling dirty plays and less time hunting for bizarre rules, the entire game could have ended differently. Even the Chiefs appeared to celebrate the cheap shot, posting a video of the hit with the caption “Dirty Dan loves making plays in the playoffs.” Hopefully, the Chiefs organization bought top-quality steaks for the referees’ guide dogs.

Browns vs. Chiefs Divisional Round Highlights | NFL 2020 Playoffs

2023 Wild Card vs the Houston Texans

This game was an unlikely endpoint of a bizarre season. The Browns broke a franchise record, starting five quarterbacks. The unlikely hero of the season was former Super Bowl MVP Joe Flacco. Flacco dramatically improved the team, helping them earn a Wild Card spot. Unfortunately, the Browns had a terrible showing in Texas. Flacco tossed a pair of pick-sixes, and Cleveland struggled on both sides of the ball. The Texans won the contest easily, 45-14.

Cleveland Browns vs. Houston Texans Game Highlights | NFL 2023 Super Wild Card Weekend

These long-standing ghosts of playoffs past still haunt the Cleveland faithful. Every time a game begins to turn, their icy hands grip your shoulders. A mocking reminder that the only sure thing in Cleveland sports is that there are no sure things.