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The Most Heartbreaking Cincinnati Bengals Moments

Over the course of 46 seasons in the NFL, the Cincinnati Bengals seem to have had more than their fair share of heartbreaking moments. We're partnering with the Cincinnati Enquirer to take a nostalgic look back at some of the toughest moments Bengals fans have had to endure through the years, from injuries to fumbles. What's the worst moment the Bengal fans have ever experienced?

We have 16 of the worst moments in Bengal history for you to relive, in no particular order. Take a look through and remember the pain of those days so you can finally let go and move forward to a brighter Bengal future. 

  • 1
    112 VOTES

    Carson Palmer Injures Knee in Playoff Game Against Pittsburgh

    Photo: user uploaded image

    Carson Palmer had been having a breakout season in 2005, passing for nearly 3,900 yards, 32 touchdowns, and boasting a 101.1 quarterback rating. On the first pass play of the Bengals' playoff game against Pittsburgh, defensive tackle Kim von Oelhoffen rolled into Palmer's knee, tearing the quarterback's ACL.

    On the same play, wide receiver Chris Henry hauled in Palmer's 66-yard pass but injured his knee as well. Despite this, the Bengals built an early 10-0 lead before giving up 24 unanswered points and turning the ball over three times. Pittsburgh won 31-17 en route to eventually winning the Super Bowl that year.
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  • 2
    104 VOTES

    Bill Walsh Gets Passed Over for Head Coaching Job, Goes to San Francisco and Wins Super Bowl Against Bengals

    Photo: user uploaded image
    This is certainly one of those cases where hindsight is 20/20. Walsh served as an assistant under legendary Bengals coach Paul Brown, where he formulated what is now known as the West Coast Offense – an offensive scheme focused on short horizontal passes in hopes of stretching out an opposing defense. Following the 1975 season, Brown retired and named Bill "Tiger" Johnson as his successor. Walsh would later say that Brown, "worked against my candidacy," to be a head coach anywhere in the NFL. In 1979, he was named head coach of the San Francisco 49ers and drafted quarterback Joe Montana from Notre Dame in the third round. Walsh would win two of his three Super Bowls against the Bengals, first in 1981 and later in 1988 and would end up being considered one of the greatest coaches in NFL history.
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  • 3
    97 VOTES

    Joe Montana to John Taylor in Super Bowl 23

    Photo: user uploaded image
    Up 16-13 with 3:20 left in the fourth quarter, it looked like the Bengals were going to win their first Super Bowl title... but if they had, then this wouldn't be part of the Most Heartbreaking Bengals Moments. Quarterback Joe Montana led the 49ers on an 11-play, 92-yard drive for the winning score – a 10-yard touchdown pass to John Taylor with 36 seconds left in the game. This ended up being 49ers coach Bill Walsh's final game and his second Super Bowl win over the Bengals (the first was in 1981). To rub salt into the wound, in 2006, NFL.com named this game the best Super Bowl game of all-time, although there have been some close ones since that list came out.
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  • 4
    42 VOTES

    Lewis Billups Dropped Interception in Super Bowl 23

    Video: YouTube
    For the better part of three quarters in Super Bowl 23, San Francisco and Cincinnati traded field goals. With less than a minute left on the ensuing kickoff, Bengals running back Stanford Jennings ran in a 93-yard touchdown, putting the Bengals up 13-6 going into the fourth quarter. The 49ers would respond on the next drive with Joe Montana hitting Jerry Rice for a 14-yard touchdown, but it was the play before this that could have turned the tide in the Bengals favor. Cornerback Lewis Billups dropped a sure interception in the end zone that would have given the Bengals the ball at the 20-yard line. San Francisco ended up winning the game 20-16 when Montana found John Taylor for a 10-yard touchdown with 36 seconds left in the game.
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