The Cincinnati Bengals are one of the few remaining teams in the NFL that have yet to win a Super Bowl trophy. The Bengals have had their fair share of mishaps and excruciating moments that has somehow landed them the nickname “The Bungles.”

Although they've been able to make the playoffs quite frequently, Cincinnati has fallen short in their quest for the coveted Vince Lombardy Trophy. Here are some of the most heartbreaking moments in the Bengals history.

1. Super Bowl XVI vs. San Franciso 49ers (Jan. 1982)

The two teams were on a similar path as both squads turned their losing records from the previous season (both at 6-10) to claim the top two spots in the regular season. The Bengals were led by NFL MVP and Comeback Player of the Year winner Ken Anderson who completed 3,754 yards for 29 touchdowns and just 10 interceptions. The quarterback spearheaded the Bengals to claim their first two playoff wins in franchise history, defeating the Buffalo Bills and the San Diego Chargers to set a matchup between the up-and-coming San Francisco 49ers.

San Francisco was a one-point favorite coming into the championship game as they won their first meeting against Cincinnati earlier that year. 49ers gunslinger Joe Montana took advantage of a few mistakes of the Bengals and brought San Francisco up 20-0 at halftime. Cincinnati, though, clawed their way back and found themselves within striking distance with a nine-point deficit with five minutes still on the clock.

At the end, San Francisco proved to be the better team with a 26-21 victory behind a record-tying four-field-goal performance by Ray Wersching.

2. Super Bowl XXIII vs. San Francisco 49ers (Jan. 1989)

Seven years after their first Super Bowl duel, the two squads were back at it again in 1989 for a rematch in Super Bowl XXIII. This was only the third time in NFL Super Bowl history that two teams would face each other again. After a controversial 1987 season where head coach Sam Wyche and quarterback Boomer Esiason, the Bengals bounced back to lead the league in the 1988 regular season in scoring, rushing yards and total yards. Esiason proved to be the right man for the job for the Bengals as he earned himself MVP honors that year. Eddie Brown and Anthony Muñoz also beefed up the Bengals' potent offensive line who had had their work cut out for them as they were again facing Joe Montana and the red-hot San Francisco squad.

It was a close toe-to-toe matchup at the Joe Robbie Stadium in Miami as both squads traded some points as the first half ended 3-3. This was the first time in Super Bowl history for the match to be tied at halftime. After a 93-yard kickoff return by running back Stanford Jennings in the third quarter, Cincinnati continued to edge their way to a 16-13 lead with over three minutes to go in the ball game. This would be a game decided by Hall of Famer Joe Montana, as he led the 49ers to an 11-play, 92-yard drive to score the winning touchdown with just 30 seconds left. The 49ers were just the sixth team in league history to win the Super Bowl over a team with a better regular-season record.

3. Wild Card Playoffs vs. Pittsburgh Steelers (Jan. 2016)

The Bengals kicked off the 2015 NFL season with a franchise-best 8-0 start. Mid-season was a bit rocky for the Bengals, as they would go on to lose a couple of crucial games in November and December. However, the glorious start for the team was enough to earn them a No. 3 spot in the AFC. This set them up with a first-round playoff matchup against division rival Pittsburgh Steelers.

It was a chippy match between the two bitter rivals as multiple penalties and bone-crushing hits were seen almost play after play. Steelers signal-caller Ben Roethlisberger manufactured his way to bring Pittsburgh to a commanding 15-o lead after three quarters before getting carried off the field with a shoulder injury. The Bengals slowly inched their way back and grabbed the lead with 16 unanswered points with under two minutes left to play behind solid plays from quarterback AJ McCarron. A few fouls by the Bengals' defense in the dying moments of the game put Steelers within field goal distance. Steelers kicker Chris Bowell knocked in a field goal from 35 yards to ultimately eliminate Cincinnati, 18-16.

The defeat was the Bengal's fifth straight first-round playoff exit, which put them in the league's record book for the wrong reasons. This was also the last playoff game of head coach Marvin Lewis as he failed to make another playoff appearance until eventually leaving in 2018.