When it comes to building winning lineups on Underdog, discipline is just as important as finding the right players. That’s why we keep our plays tight—sticking to just 3 legs. The math backs it up: the more legs you stack, the faster your odds drop. For example, even if each leg has a 60% chance of hitting (better than a coin flip), a 3-leg entry still has a 21.6% chance of cashing. Add a fourth leg, and it plummets to 12.9%. By the time you’re at 5 legs, you’re looking at just 7.7%—not exactly a recipe for consistency. In other words, chasing big payouts with long slips might look appealing, but the sharp strategy is keeping it short and maximizing your actual chances of walking away with a win. We have also partnered with my friend David, the creator of PropsBot.AI, to bring you picks that I like personally and are backed up by data driven insights! Click the link underlined here to get a free 10-Day trial of PropsBot.AI and find more picks and values for yourself!
RJ Harvey HIGHER THAN 0.5 Rush+Rec TDs
RJ Harvey Over 0.5 TDs is exactly the type of underdog spot we want to attack. Harvey didn’t find the end zone last game, but that doesn’t erase the fact that he scored 6 touchdowns in the five games prior—this is a proven red-zone weapon, not a fluke scorer. Last week we easily cashed our Travis Etienne prop by picking on a soft Buffalo run defense, and this matchup sets up in a similar way. With Bo Nix dealing with a sophomore slump, this offense has clearly leaned into its identity: defense, ball control, and pounding the run game. That game script heavily favors RJ Harvey, especially near the goal line. Given his recent scoring stretch and role in this offense, it honestly feels more likely Harvey scores multiple touchdowns than gets shut out entirely, making Over 0.5 TDs a strong underdog play.
Matt Stafford HIGHER THAN 267.5 Pass Yds
This checks every box we look for in an underdog-style over. Stafford has cleared this number in 7 of his last 10 games, and the matchup only boosts his ceiling. The Chicago Bears rank 25th against the pass, and we’ve already seen how this defense struggles when facing real firepower through the air. The last time they matched up with an elite receiving duo was against the Cincinnati Bengals, where they surrendered 470 passing yards to Joe Flacco. That’s a massive red flag. With volume likely baked into the game script, Matt Stafford should be throwing early and often, making 300 yards very much in play. Add in the fact that PropsBotAI tags this as their favorite bet of the week of ours with a 64.5 confidence score and a 5% edge, and this over stands out as one of the strongest passing props on the board.
Colston Loveland HIGHER THAN 4.5 Receptions
Colston Loveland HIGHER THAN 4.5 Receptions is a volume-driven play that continues to age better by the week. Loveland has seen double-digit targets and hauled in 6+ catches in each of his last three games, firmly establishing himself as a centerpiece of this passing attack. What’s changed is how Caleb Williams is distributing the ball—he’s no longer forcing targets to DJ Moore, and that shift has been a clear net positive for Colston Loveland and the Chicago Bears offense as a whole. If this game tilts toward shoot-out territory, Loveland’s role over the middle becomes even more valuable. We’re not asking for anything extreme here—just one more catch than one per quarter. When you zoom out and look at Loveland’s usage trend, the steady uptick in targets and involvement makes it clear: he’s becoming a focal point, and that gives this over real confidence.
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