At this point in the NFL offseason, there are many unanswered questions. Most of these questions can only be answered by time, but many of us use speculation to get us through these dry months.

That speculation can come in many forms, and I’ve even participated in it myself. It could be player rankings, projected starting lineups, or even which free agents teams will target before training camp.

For the Dallas Cowboys, there are many questions after the miserable end to the 2023 NFL season at the hands of the Green Bay Packers.

The 48-32 home loss to the 7th-seeded Packers sent many fans into a state of shock and bewilderment followed by anger. Why can’t this team get over the hump? How could they have been so unprepared to play?

Like with the unceremonious end to any season, there was a scapegoat and his name is Dan Quinn. The Cowboys turned in their worst defensive performance of his time in Dallas on that fateful day in January.

Quinn knew his time was up and he accepted the head coach position with the Washington Commanders. He then poached several players from the Cowboys to boot.

Today, I want to use speculation to determine the toughest three contests on the Cowboys’ 2024 schedule. Tomorrow I will rank the three easiest, but for today let’s discuss their three toughest opponents.

Several factors went into these rankings. Not only the opponent. We have to take into consideration the time of year, the location, and even the weather.

I’ve decided to exclude both of the Eagles games from this list, although the matchup in Philadelphia would have likely ranked 3rd.

3. Week 1 @ Cleveland Browns

The Cowboys start off the season with an immediate challenge in the form of the Cleveland Browns. Cleveland hasn’t been able to put it all together recently, but they have some pieces that pose problems for opposing teams.

Cleveland’s strength, despite weapons like Amari Cooper and Nick Chubb at Deshaun Watson’s disposal, is the defense led by All-Pro Myles Garrett.

Garrett will be licking his chops to line up across from Cowboys rookie LT Tyler Guyton, who is favored to win the job vacated by Tyron Smith. It will be Guyton’s first NFL game experience and the Cowboys must do everything in their power to help him.

The Browns defense is fierce behind Garrett as well. Other players like Za’Darius Smith, Denzel Ward, and Devin Bush round out the rest of the defense.

Dallas will need to do their best to run the football to limit Garrett’s opportunities to rush the passer. Will they be able to run the ball? That’s the question that needs to be answered before we can say the Cowboys will leave Cleveland with a victory.

2. Week 3 vs Baltimore Ravens

The Cowboys only play vs the AFC North once every four years. They face three of the four division opponents within the first five weeks of the season.

That division is known for its toughness and physicality, something the Cowboys have been lacking for as long as I can remember. Baltimore will be a tougher challenge than the Browns because they have more talent.

Reigning MVP Lamar Jackson is a menace on the field and is difficult to get down, especially when the play breaks down. He has weapons like RB Derrick Henry, wide receivers Zay Flowers and Rashod Bateman, and TE Mark Andrews.

Dallas will have to play extremely disciplined, something they have relatively failed to do over the past few years. Baltimore capitalizes on mistakes and their offense can score in bunches.

The Cowboys will have to hit them early and often, keeping mistakes to a minimum if they hope to avoid embarrassment on their home turf.

1. Week 7 @ San Francisco

In the #1 spot, a familiar nemesis makes an appearance. The Cowboys have not had much success versus the San Francisco 49ers recently, but that could all change. Or not.

The fanbase’s confidence versus the 49ers was shattered by last year’s shellacking. In the most hyped game (at the time) of the 2023 season, the 49ers showed the Cowboys didn’t even belong on the same field.

Dak Prescott and the offense couldn’t get anything going offensively, mustering 10 points total, and just three points by halftime.

San Francisco had their way in a 42-10 beatdown that removed any confidence I had against that team. That lack of confidence is still there today. We are at a point where we don’t think this version of the Cowboys can defeat this version of the 49ers until we see it happen.

The 49ers are atop the NFC and looking to defend their conference championship. Dallas does get to face them with an extra week to prepare (bye week), but not even that fact brings me any relief.

San Francisco is the boogeyman for the Cowboys currently and until they prove otherwise, the 49ers are the toughest game on their 2024 schedule.