During the strike-shortened1987 season, quarterback Boomer Esiason and head coach Sam Wyche had openly feuded, and the team finished with a miserable 4–11 record. Esiason and Wyche worked out their differences in the off-season. In 1988 Esiason ended up having the best season of his career en route to Super Bowl XXIII. During the regular season, he threw for 3,572 yards and 28 touchdown passes with only 14 interceptions, while also rushing for 248 yards and a touchdown on 43 carries. Esiason's performance made him the top rated quarterback in the league with a 97.4 passer rating and earned him the NFL Most Valuable Player Award.
Cincinnati had a number of offensive weapons, boasting 6 Pro Bowl selections. Wide receiver Eddie Brown was the top receiver on the team, with 54 receptions for 1,273 yards and 9 touchdowns, setting franchise records for most receiving yards in season, highest yards per catch average in a season (24.0) and most receiving yards in a single game (216 against the Pittsburgh Steelers). Wide receiver Tim McGee and Pro Bowl tight end Rodney Holman were also major threats, combining for 75 receptions, 1,213 yards, and 9 touchdowns.
Rookie fullback Ickey Woods was Cincinnati's top rusher with 1,066 yards and 15 touchdowns, while also catching 21 passes for 199 yards. Woods gained a lot of media attention with his "Ickey Shuffle", a dance routine he did in the end zone to celebrate his touchdowns. Multi-talented running back James Brooks was also a key contributor, gaining a total of 1,218 combined rushing and receiving yards and 14 touchdowns.
The Bengals' offensive line was led by such Pro Bowl players as right guard Max Montoya and left tackle Anthony Muñoz. Muñoz was named the NFL Offensive Lineman of the Year for the third time in his career, and was selected to play in the Pro Bowl for the 8th consecutive season. The Bengals' pioneering use of the Hurry-up offense was perfected that year, making it difficult for defenders to respond to plays and make proper substitutions. With all these weapons, Cincinnati's offense led the NFL in scoring (448 points), rushing yards (2,710), and total yards (6,302).
The Bengals defense ranked 17th in the league, allowing 5,556 yards and 329 points during the regular season. Cincinnati had a superb defensive line, led by Pro Bowl defensive tackle Tim Krumrie, along with linemen Jim Skow (9.5 sacks), David Grant (5 sacks), and Jason Buck (6 sacks). Pro Bowl defensive backs Eric Thomas and David Fulcher combined for 12 interceptions. The team ended up winning the AFC Central with a 12 – 4 record.
The Bengals would get off to a fast start, coming from behind to beat the Phoenix Cardinals 21-14, and then they would sweep a 2-week road trip in Pennsylvania, coming from behind to beat the Philadelphia Eagles 28-24 and the Pittsburgh Steelers 17-12 in weeks 2 and 3. The Bengals would then beat the Cleveland Browns at home 24-17 to start 4-0 for the first time since 1975. The Bengals would then thump the Raiders in Los Angeles 45-21 (the Bengals first road win against the Raiders in 9 tries), and then would beat the New York Jets 36-19 at home to start 6-0, tying the franchise best start to a season at the time. In week 7 the New England Patriots would provide the Bengals with their first loss of the season, 21-27. Boomer threw for 5 interceptions which was featured on Showtimes Inside the NFL season 10 episode 12.
In week 10, the Bengals destroyed the Pittsburgh Steelers 42-7 at home to set the records in the series for largest margin of victory and most points scored by one team in the series. It would also be the first of 3 straight season sweeps of the Steelers for the Bengals.
In week 14, the Bengals beat the Buffalo Bills 35-21, handing Buffalo only their second loss of the season. The Bills had come into the game with an 11-1 record and the overall best record in the NFL.
The AFC Champion Bengals were to play the San Francisco 49ers in Super Bowl XXIII. On the evening of January 21, 1989, the night before the game, Stanley Wilson told the coaching staff that he had left his playbook in his hotel room before a team meeting. When he was fifteen minutes late, his position coach, Jim Anderson, looked for Wilson. Anderson found Wilson crumpled on the bathroom floor of his hotel room with cocaine next to him. Later that night, he slipped away from a Bengal staffer who was watching him and got more cocaine. No one from the Bengals heard from him again until the day after the game.
Tim Krumrie may perhaps be best known for suffering one of the most dramatic football injuries ever televised, a shattered leg during Super Bowl XXIII. Although it was reported at the time and widely believed that his foot caught in the grass, causing the break, a Cincinnati videographer had the best angle, and the breaks to Krumrie's leg occurred when San Francisco running back Roger Craig's knee smashed through both lower leg bones. Krumrie suffered two breaks in his tibia and another in his fibula.
Seattle's defense completely shut down Bengals quarterback Boomer Esiason, the NFL's top rated quarterback and MVP during the season, limiting him to just 7 of 19 completions for 108 yards. But they were unable to contain Cincinnati on the ground. The Bengals recorded 254 rushing yards (126 of them and a touchdown from fullback Ickey Woods), while holding the Seahawks to 22.
Cincinnati jumped to a 21–0 halftime lead with Woods' score and two from running back Stanley Wilson. Meanwhile, the Seahawks could only manage 47 total yards in the first half. But after a scoreless third quarter, Seattle attempted a comeback. First, quarterback Dave Krieg threw a 7-yard touchdown pass to John L. Williams, who finished the game with 11 receptions for 137 yards. Then Krieg scored on a 1-yard quarterback sneak. However, Norm Johnson missed the extra point attempt and Seattle was unable to score again.
The Bengals forced 3 interceptions, and allowed only 45 rushing yards and 136 passing yards, while their offense held the ball for 39:29. Bills starting running back Thurman Thomas was held to just 6 yards on 4 carries, while quarterback Jim Kelly completed only 14 of 30 passes for 161 yards and 1 touchdown, with 3 interceptions. Just like their previous game, the Bengals didn't get much of a performance from NFL MVP Boomer Esiason, who completed only 11 of 20 passes for 94 yards, with 1 touchdown and 2 interceptions. But once again, their running game was able to pick up the slack, gaining 175 yards on the ground, 102 yards and 2 touchdowns coming from fullback Ickey Woods.
Cincinnati took a 7–0 lead in the first quarter after defensive back Eric Thomas' interception set up Woods' 1-yard touchdown. Kelly led the Bills back with 4 consecutive completions, the last one a 9-yard touchdown pass to wide receiver Andre Reed. Then after forcing a punt, Buffalo drove to the Bengals 26-yard line, only to have Scott Norwood miss a 43-yard field goal attempt. Following another punt, Kelly was intercepted again, this time by defensive back Lewis Billups, and the Bengals capitalized with running back James Brooks' 10-yard touchdown reception from Esiason. Later on, Bills defensive back Mark Kelso intercepted a pass from Esiason and returned it 25 yards, setting up a 39-yard field goal by Norwood to cut the Bills deficit to 14–10 by halftime.
The Bengals took over the game in the second half, forcing Buffalo to start all of their drives from inside their own 23-yard line and holding them to 53 yards, 2 first downs, and 0 points. Late in the third quarter, Bengals running back Stanley Wilson gained 6 yards on a fake punt attempt, and Cincinnati drove to score on Woods' second touchdown of the game, increasing their lead to 21–10. The Bills responded with a drive into Bengals territory, but safety David Fulcher picked off a desperate fourth down pass from Kelly in the end zone.
This was the last time the Bengals defeated the Bills until Week 4 of the 2011 season. The Bills would go on to win 10 straight against them.
The game started out with devastating injuries on both sides. On the third play of the game, 49ers tackle Steve Wallace was taken off the field with a broken ankle. Later on, Bengals defensive lineman Tim Krumrie twisted his ankle nearly 180 degrees, shattering two bones in his left leg. Although it was reported at the time and widely believed that his foot caught in the grass, causing the break, a Cincinnati videographer had the best angle, and the breaks to Krumrie's leg occurred when San Francisco running back Roger Craig's knee smashed through both lower leg bones. Krumrie suffered two breaks in his tibia and another in his fibula.
After the two teams traded punts on their first drives of the game, the 49ers, aided by a roughing the passer penalty and a 17-yard screen pass to Tom Rathman on 3rd-and-10, marched 73 yards from their own 3-yard line to the Bengals 24. But dropped passes, including one by receiver Mike Wilson on the 2-yard line (the first time in a Super Bowl that instant replay was used to reverse a call), forced them to settle for a 41-yard field goal from kicker Mike Cofer.
On the 49ers next drive, Montana threw a pass to wide receiver Jerry Rice, who first tipped it to himself and then made a one-handed catch before stepping out of bounds at the San Francisco 45-yard line. Then after reaching the Cincinnati 42-yard line, Montana spotted defensive back Lewis Billups trying to cover Rice one-on-one and made him pay for it by completing a pass to the receiver at the 10. But two plays later on a third down play, Bengals safety David Fulcher made a touchdown saving tackle at the 2-yard line to keep full back Tom Rathman from scoring. Cofer then attempted a 19-yard field goal, but a poor snap from center Randy Cross (though NBC's Dick Enberg initially blamed backup guard Chuck Thomas; who lined up next to Cross) threw off the kicker's timing and his kick sailed wide left. It became the shortest missed field goal in Super Bowl history.
The 49ers then forced the Bengals to punt on their next drive. On the play, San Francisco Pro Bowl punt returner John Taylor misplayed punter Lee Johnson's kick, and it sailed over his head, bouncing all the way to the 49ers 9-yard line to make it a Super Bowl record 63-yard punt. But Taylor made up for his mistake by chasing the ball down and returning it for a Super Bowl record 45 yards to the Bengals 46-yard line. Thanks to Taylor, a seemingly routine punt had turned into a double record setter.
However, the 49ers were unable to take advantage of their excellent starting field position. On first down, running back Harry Sydney fumbled a pitch from Montana and was downed for a 10-yard loss after he dove on the ball. On the next play, Montana was sacked by defensive lineman David Grant. Then on third down, Fulcher forced a fumble from 49ers running back Roger Craig, and Bengals defensive end Jim Skow recovered the ball on his own 41-yard line. Cincinnati then drove to the San Francisco 42-yard line, but after 2 incomplete passes and defensive end Danny Stubbs's 8-yard sack on Bengals quarterback Boomer Esiason, they were forced to punt. However, Johnson pinned the 49ers back at their own 11-yard line with his punt. Then the Cincinnati defense limited the 49ers to just 1 yard on their ensuing drive, and ended up with great field position after defensive back Ray Horton returned San Francisco punter Barry Helton's 37-yard punt 5 yards to the 49ers 44-yard line
On their ensuing drive, the Bengals managed to get into scoring range by driving 28 yards to the San Francisco 16-yard line, assisted by an 18-yard completion from Esiason to receiver Tim McGee. But after Esiason's third down pass intended to wide receiver Eddie Brown was overthrown, they were forced to settle for kicker Jim Breech's 34-yard field goal with 1:15 left in the half.
The two teams went into their locker rooms tied 3 – 3, the first halftime tie in Super Bowl history, and the lowest halftime score since the Pittsburgh Steelers took a 2 – 0 halftime lead over the Minnesota Vikings in Super Bowl IX.
On their opening possession in the second half, the Bengals managed to get a sustained drive going, moving the ball 61 yards in 12 plays and taking 9:15 off the clock. Esiason, who completed only 4 of 12 passes for 48 yards in the first half, completed 3 of 4 passes for 54 yards on the drive, including a 20-yard completion to James Brooks and 23-yard and 11-yard completions to Cris Collinsworth, setting up a 43-yard field goal from Breech to give the Bengals their first lead of the game, 6–3. Cincinnati then forced San Francisco to punt, but on the first play of their next drive, 49ers rookie linebacker Bill Romanowski intercepted a pass from Esiason at the Bengals' 23-yard line. However, after a dropped pass by Jerry Rice, the 49ers offense could not get a first down, and they had to settle for Cofer's 32-yard field goal to tie the game.
With less than a minute left in the third quarter, it appeared that this would become the first Super Bowl ever to go 3 quarters without either team scoring a touchdown. But on the ensuing kickoff, Bengals kick returner Stanford Jennings returned the ball 93 yards for a touchdown to give the Bengals a 13 – 6 lead. Jennings would be the second player to return a kickoff for a touchdown in Super Bowl history. In four games played at Joe Robbie Stadium, each game had a kickoff return for a score, all by the eventual losing team.
But the 49ers immediately responded with a touchdown of their own, on an 85-yard, 4-play drive. First, Montana threw a short pass to Jerry Rice, who turned it into a 31-yard gain. Then the San Francisco quarterback completed a 40-yard pass to Craig on the first play of the 4th quarter, moving the ball to the Bengals 14-yard line. Montana's next pass was nearly intercepted but dropped by Billips in the endzone. Montana then threw a 14-yard touchdown pass to Rice, and the game was tied, 13 – 13.
Cofer's ensuing kickoff went out of bounds, giving the Bengals the ball at their own 35-yard line. But they could only reach the 43-yard line before being forced to punt. Taylor nearly turned the ball over by fumbling Johnson's punt, but his teammate Darryl Pollard recovered the ball at the San Francisco 18-yard line. On the first play of the ensuing drive, Montana completed a 44-yard pass to Rice, and then Craig ran for 7 yards, moving the ball to the Bengals 31-yard line. But after Craig was tackled for a 1-yard loss on the next play, Fulcher broke up a third down pass intended for Taylor, and then Cofer's ensuing 49-yard field attempt sailed wide right.
The Bengals took over from their own 32-yard line following the missed field goal, and retook the lead with a 10-play, 46-yard drive, featuring a 17-yard reception by backup receiver Ira Hillary on third down and 13, along with 21 yards on three carries from Ickey Woods and a 12-yard play-action sideline pass to James Brooks. At the end of the drive, Breech kicked a 40-yard field goal, giving the Bengals a 16–13 lead with 3:20 left in the game. The 49ers returned the ensuing kickoff to their own 15-yard line with 3:10 on the clock, but an illegal block penalty on the play pushed the ball back half the distance to the goal line to the 8.
Montana then led an 11-play, 92-yard drive to score the winning touchdown. In order to calm his teammates in the huddle just before the final game-winning drive, Montana pointed into the stadium crowd and said "Hey, isn't that John Candy?" The moment worked, and the 49ers were able to drive down the field for the win. It became the defining moment of Montana's "Joe Cool" reputation. Assuming that the Bengals would expect him to throw the ball near the sidelines (to enable the receivers to step out of bounds to immediately stop the clock), Montana first threw a pair of completions in the middle of the field, one to Craig and one to tight end John Frank. His next pass went 7 yards to Rice, which was then followed up by a pair of runs by Craig to reach their own 35-yard line. Montana then completed a 17-yard pass to Rice to advance the team to the Bengals 48-yard line, and followed it up with a 13-yard completion to Craig to move them to the 35-yard line.
But on the next play, Montana threw his first incomplete pass of the drive. After that, Cross committed an illegal man downfield penalty, which at the time was a 10-yard foul, moving the ball back to the 45-yard line and bringing up second down and 20 to go with just 1:15 left in the game. But Montana overcame the situation on the next play with a 27-yard completion to Rice, who caught the ball at the 33, evaded 3 Bengal defenders, and ran to the 18-yard line before Rickey Dixon managed to tackle him to prevent a touchdown. An 8-yard pass to Craig then advanced San Francisco to the 10-yard line. Then with 39 seconds left in the game, Montana finished the drive with a 10-yard touchdown pass to Taylor, giving the 49ers the lead for good. Finally, San Francisco's defense sealed the victory after Esiason's pass to Collinsworth was broken up as time expired.
The most 100-yard rushing games in a Bengals season is seven, during the 12–4 season of 1988. Ickey Woods had five while James Brooks had two. Ickey Woods set the franchise record for most rushing yards in a postseason game when he rumbled for 126 yards in Cincinnati's 21–13 victory over Seattle in the AFC Divisional Playoffs (Dec. 31).