Underdog Pick Em: Week 5

Let's have some fun and try to win a few dollars this season. Here's how this article will work: each week, I'll share my favorite player props, put my own real money behind them, post a screenshot of the bets, and explain why I like each pick. Sometimes the reasoning will come from deep statistical analysis, and other times it'll just be a gut call. For every pick, I'll walk you through my thought process. If it makes sense to you, feel free to tail me.

The goal is simple: end the week with more money in my Underdog account than I started with. At the same time, this is meant to be recreational, geared toward anyone who wants to add a little excitement to the games with a small bet. Most of the picks will lean toward overs, because overs are simply more fun to root for. All else being equal, I'll try to focus on prime-time games and the most entertaining spots on the schedule. However, I won't force plays just to have action on every night game.

How It Works

Underdog Pick'em is a fun twist on daily fantasy games where you predict whether a player will go higher or lower than their projected stats across categories like touchdowns, yards, or fantasy points. To play, simply pick at least two props from two different teams. You can choose player stats like touchdowns, rushing yards, or even fantasy points and predict whether they will go higher or lower than the projected numbers.

Payouts

Underdog Fantasy offers a payout structure that rewards you based on the number of correct selections:

• Two picks: 3x your entry
• Three picks: 6x your entry
• Four picks: 10x your entry
• Five picks: 20x your entry

Tracking Last Week

I will track every Pick Em I make this season and start each week's article with a quick review of what went wrong and what went right the previous week. 

• Last Week (1-3), -$40
• Season (13-15), -$128

Lamar Jackson hit his rushing yardage over (46.5) despite leaving the game early. However, Patrick Mahomes II came in well under his rushing yardage total (24.5) in a game that ended up being surprisingly uncompetitive. While it was the Chiefs/Mahomes half of the Pick Em that didn't hit, it feels more like the Ravens offense let us down by not pushing Kansas City.

I'm going to retire TreVeyon Henderson props after a third over failed to hit by just a few yards. His 14 receiving yards last were 3.5 short of his total. I may have been a week early on Wan'Dale Robinson, who did very little in Jaxson Dart's debut.

Week 5 Picks

Pick 1

David Montgomery

• I am leaning into a narrative angle here. Montgomery is from Cincinnati, and this will be his first game in his hometown since high school. His sister is paralyzed, and this will be the first time she has been able to see him in person in years. If Detroit controls the game, the coaches may look to reward him late.

For @SideLionReport

Lions running back David Montgomery will make his return to his hometown for the first time in his NFL career. Sunday's game will be extra special and filled with emotions for Montgomery.#DetroitLions #OnePride https://t.co/qcsv7JsUwE

— Caden Handwork (@cadenhandwork17) October 2, 2025

• Even without the narrative, this is a strong spot. The Bengals have given up 1.5 touchdowns per game to opposing running backs. Detroit is an 8.5-point road favorite with a team total of 28.5.

• Montgomery has scored in 16 of his last 22 games (72.7%).

Jameson Williams

• It feels like Williams is due. He is playing over 85% of the snaps and saw a season-high eight targets last week, though he struggled against the Browns' defense. Williams has a 44.7% share of team air yards and is running a route on 92% of Jared Goff's dropbacks. This is going to click.

• Williams has topped 50 receiving yards in 11 of his last 19 games (58%).

Jameson Williams had 195 unrealized air yards in Week 4.

That's the third-highest single-game mark since 2022. Three games with under 50 yards to start the season certainly not ideal, but Lions are trying — Bengals up next

— Ian Hartitz (@Ihartitz) September 29, 2025

• Cornerback play is one of Cincinnati's biggest problems. Cam Taylor-Britt was benched last week after five bad snaps. The Bengals have allowed the seventh-most receiving yards to opposing wide receivers (659), and that number could be much higher if not for early blowouts and drops in the first two weeks.

Ja'Marr Chase

• As with Montgomery, I am leaning into a narrative angle. Chase is the face of the franchise with Joe Burrow out, and he has shouldered the tough questions after back-to-back blowouts. He was openly frustrated with the play calling last week as the Bengals ran Chase Brown into loaded boxes on first down.

• Zac Taylor is coaching for his job. He needs the team to play better and needs to make sure his best player is bought in. Plus, Chase is getting open, and Jake Browning will be made well aware of that fact in team meetings this week.

Ja'Marr Chase had a step or more of separation on 40% of his routes vs Denver (13 of 32 routes). He only saw 4 targets on those open routes.

6 gotta get him the ball when he's open in space.

— Andrew Russell (@Andrew_Russell7) October 1, 2025

• Chase has at least 86 receiving yards in each of his last four home games. The matchup looks favorable to keep that streak alive.

Ja'Marr Chase goes from MIN and DEN to the Lions, who now don't have CB1 D.J. Reed (IR) with other CBs on IR. FS Kerby Joseph (knee) hasn't practiced either.

Amik Robertson pushing from slot to the outside. Terrion Arnold has been targeted often. Avonte Maddox in the slot.

— Hayden Winks (@HaydenWinks) October 3, 2025

Chase Brown

• Brown has seen at least three targets in 12 straight games and is averaging 6.3 yards per target in his career.

• The Bengals' running game is difficult to trust, but the team is high on Brown. Expect Dan Pitcher to get more creative in using him, especially as a pass catcher.

Pick 2