For much of the last decade, the San Francisco 49ers have been one of the NFL’s most consistent contenders under head coach Kyle Shanahan. Since taking over in 2017, Shanahan has transformed the franchise into a perennial Super Bowl threat, guiding the team to multiple NFC Championship appearances and two Super Bowl berths. Yet despite all the success, one narrative continues to follow him: heartbreaking playoff defeats.
While Shanahan has built championship-caliber rosters, several crushing postseason losses have prevented the 49ers from reaching football immortality. Here’s a ranking of the five most painful playoff losses of the Shanahan era.
5. NFC Championship Game Loss vs. Rams (2021 Season)
The 49ers entered the NFC Championship against the Los Angeles Rams with confidence after defeating their division rival six consecutive times. San Francisco even held a 17-7 lead in the fourth quarter.
However, the offense stalled, Matthew Stafford engineered a comeback, and the Rams escaped with a 20-17 victory. To make matters worse for 49ers fans, Los Angeles went on to win the Super Bowl just weeks later.
4. NFC Championship Game Loss vs. Eagles (2022 Season)
This game was heartbreaking for a completely different reason. The 49ers barely had a chance to compete after quarterback Brock Purdy suffered an early elbow injury.
Without a healthy quarterback, San Francisco’s offense became one-dimensional, and the Eagles cruised to a 31-7 victory. Fans were left wondering what might have happened if the team had been healthy.
3. Super Bowl LIV Loss vs. Chiefs (2019 Season)
The 49ers were just minutes away from ending their championship drought.
Leading the Kansas City Chiefs 20-10 late in the fourth quarter, San Francisco appeared destined to capture its sixth Lombardi Trophy. Instead, Patrick Mahomes delivered one of the greatest comeback performances in Super Bowl history, scoring 21 unanswered points to stun the 49ers 31-20.
For many fans, this remains the moment when a championship slipped through their fingers.
2. NFC Championship Game Loss vs. Seahawks (2013 Season)
Although this defeat occurred while Shanahan was the offensive coordinator rather than head coach, it remains one of the most painful losses associated with his playoff career.
The game ended with Richard Sherman’s iconic deflection and interception, sending Seattle to the Super Bowl while crushing San Francisco’s title hopes. It marked the end of one of the franchise’s greatest eras without a championship.
1. Super Bowl LVIII Loss vs. Chiefs (2023 Season)
No playoff loss has hurt more than Super Bowl LVIII.
The 49ers held multiple opportunities to defeat Kansas City, including a fourth-quarter lead and possession in overtime. Yet Mahomes once again delivered under pressure, leading the Chiefs to a dramatic 25-22 victory.
Unlike the 2019 Super Bowl, this defeat felt even more devastating because San Francisco was viewed as the more complete team. The loss reinforced questions about whether Shanahan’s talented squads can finally finish the job on football’s biggest stage.
Can Kyle Shanahan Finally Break Through?
Despite these painful memories, Shanahan remains one of the NFL’s elite coaches. Few franchises have enjoyed the level of sustained success the 49ers have achieved under his leadership. However, championships are the ultimate measuring stick in professional sports.
As another season approaches, the pressure is mounting. San Francisco has the talent, the experience, and the motivation to return to the Super Bowl. The only thing missing is the championship that has repeatedly slipped away.
For 49ers fans, the hope remains the same: that the next playoff run will finally erase the heartbreak of the previous five.