Every NFL franchise has had its ups and downs over the years while the Tennessee Titans are no exception. However, there have been many more lows than highs for the Titans since the franchise officially made the move from Houston to Nashville more than 20 years ago.

The Titans have certainly hit some bumps in the road through some seriously rough stretches throughout the team's history, though there are three moments in particular that definitely still haunt Tennessee fans a bit more than most — even to this day. Heartbreaking may not be a strong enough phrase for at least one of the following moments in Titans history while all three unfortunately deserve to be on such a list.

1999-00: Super Bowl XXXIV Loss to St. Louis Rams

The Tennessee Titans can arguably make a claim for the most heartbreaking moment in NFL history — in the team's inaugural season at that! Right up there with the most heartbreaking moments in recent sports history as well, the Titans literally lost Super Bowl XXXIV to the St. Louis Rams by one yard as time expired.

After producing the “Music City Miracle” against the Buffalo Bills to open the playoffs before defeating the rival Indianapolis Colts in the divisional round, the Titans trounced another divisional foe in the Jacksonville Jaguars in the AFC Championship Game en route to a matchup against the aforementioned Rams. As a result, the Titans were riding extremely high after defeating the Jaguars for a third time in 1999-00, a campaign that saw Jacksonville go a perfect 14-0 against the rest of the league. However, the high-powered Rams were simply too much for the Titans to handle in the end, though Tennessee managed to keep the game close throughout with the team's defense impressing versus a now infamous St. Louis offense.

In the end, Rams linebacker Mike Jones tackled Titans wide receiver Kevin Dyson on the one-yard line as time expired with St. Louis hanging on to win the game by the score of 23-16. The Titans have not been back to the Super Bowl since while the franchise has never won a title.

2008-09: Divisional Round Playoff Loss to Baltimore Ravens

In 2008-09, the Tennessee Titans came out of nowhere while producing a stellar 13-3 regular season record, good for the No. 1 seed in the AFC playoff picture. Despite the fact that the Titans lost starting quarterback Vince Young to a season-ending injury in Week 1 of the regular season, a veteran signal caller in Kerry Collins in addition to the two-headed monster in the backfield in running backs Chris Johnson and LenDale White led the way for Tennessee, who started the year a perfect 10-0. With a first round bye all wrapped up, the Titans ultimately hosted the always dangerous Baltimore Ravens in the divisional round of the playoffs.

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Even though the Titans were well rested, playing at home and had already defeated the Ravens during the regular season by the score of 13-10, Tennessee's magical season came to a screeching halt against Baltimore. Thanks to an injury to the aforementioned Johnson that cost him the second half coinciding with more than a few atrocious calls from the officials, the Ravens escaped Nashville with a 13-10 victory as a result of a game-winning field goal from kicker Matt Stover.

Adding to the forgetable outing in “Music City,” the Pittsburgh Steelers went on to win the Super Bowl in 2008-09 with Tennessee absolutely dismantling the AFC North franchise at home earlier in the year.

2019-20: AFC Championship Game Loss to Kansas City Chiefs

The Tennessee Titans encountered quite the back-and-forth season in 2019-20 as the campaign featured stretches of losing, a change under center and the AFC South franchise just barely sneaking into the postseason as the AFC's sixth and final seed. However, the Titans caught fire at the perfect time while defeating two of the best teams in the entire NFL in back-to-back weeks.

First, the Titans went on the road to seemingly end the New England Patriots dynasty and quarterback Tom Brady's time with the heralded franchise. For an encore performance, the Titans clocked yet another road win while this time taking down a longtime rival in the Baltimore Ravens, who were coming off a bye week as the AFC's top seed in 2019-20. Unfortunately, this tremendous stretch for the Titans would come to an end at Arrowhead Stadium as the eventual Super Bowl Champion Kansas City Chiefs would post a momentous comeback against the Titans in the AFC Championship Game.

The Titans not only defeated the Chiefs and former league MVP and quarterback Patrick Mahomes during the regular season, but even held a double-digit lead over Kansas City in the first half back in January.