SF 49ers: Ranking the 5 biggest disappointing seasons in team history

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San Francisco 49ers quarterback Steve Young (8) is sent airborne by Arizona Cardinals cornerback J.J. McCleskey (R) (Photo by MIKE FIALA/AFP via Getty Images) /

No. 1: SF 1999 49ers (4-12)

The No. 1 most disappointing season in Niners history is also awfully infamous.

If, for nothing else, because it marked the premature end of a Hall of Famer’s career.

With 2020 marking an injury-riddled campaign as a disappointment, the 1999 season-ending injury suffered by quarterback Steve Young in Week 3 against the Arizona Cardinals on Monday Night Football.

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Young suffered a blindside hit by Cardinals cornerback Aeneas Williams, and that proved to be the last play in the quarterback’s career.

San Francisco was originally projected to get back into the playoffs and potentially make it to the Super Bowl that season. After all, the season before, the SF 49ers finally got over the “playoff hump” by defeating the Green Bay Packers in dramatic fashion. And they boasted two elite wide receivers, Jerry Rice and Terrell Owens, to add to Young’s arsenal.

Instead, Young’s injury prompted the Niners to try getting something out of backup quarterbacks Jeff Garcia and Steve Stenstrom, which didn’t work out well.

While Garcia would eventually have his own success in San Francisco, the SF 49ers lost eight of their following nine games and would finish a disappointing 4-12, marking the first losing season since 1982.

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More importantly, the year marked the final time fans saw Young in a Niners uniform.