Chasing upsets in the sports betting world can be more profitable than you might think. Had you hopped on the Cleveland Cavaliers at +110 in their game seven in Boston on Sunday, you would have seen solid value.
You could have done the same a few days ago when the Houston Rockets were mild underdogs in a game five against the Golden State Warriors.
The betting value wasn’t through the roof for either of these spots, but it’s a great way to see how situational betting can return value with underdogs.
It can also be a ton of fun. Fun and profit don’t always work together in the sports betting world, but each week, I like to try and identify at least a few spots where it absolutely could.
Let’s take a look back at how things unfolded last week before looking at some of this week’s top underdog picks.
I tried to locate a few solid upset picks last week in the hope of building on a weak 11-18-1 upset picks record. Here’s how things went:
Darren Till over Stephen Thompson+140
Houston Rockets over Golden State Warriors+390
Seattle Mariners over Oakland Athletics+155
Washington Capitals over Tampa Bay Lightning+128
Arizona Diamondbacks over Milwaukee Brewers+127 
As you can see, last week was pretty great for my upset sports picks.
Darren Till earned the unanimous decision victory against Stephen Thompson, which I felt was doable due to his ferocity, overall talent, and torrid undefeated winning streak.
Thompson is a tough fighter, and he lasted until the end, but Till was always an odd underdog and delivered a nice +140 price.
The Rockets wound up losing their Western Conference Finals series to the reigning champs on Monday night, but before that happened, they brought back insane value (+390) in a game four win.
That gave me easily my top win of the week and one of my best victories of the young upset pick season.
I also nailed an MLB series winner with the rival Mariners topping the Athletics. The series was really tight, and Oakland did steal one win, but the M’s offered more value in the end and pulled it out for me.
The same goes for the Capitals, who edged out the Lightning to reach the 2018 Stanley Cup Finals.
You didn’t have much wiggle room for that game, but Washington felt like the more balanced team and offered a solid +128 price in a tense setting.
After going up 2-0 to start the series and winning game six to force game seven, the Capitals felt like the right call, and they made me look smart.
I needed a big week after getting off to a sluggish start, and if you went along with my upset picks, you earned a 4-1 record and probably a decent amount of cash.
That stout showing lifted my season underdog picks record to 15-19-1 and sends me into a new week with confidence. Let’s get into this week’s picks.
The Golden Knights are the understandable favorites heading into game two of the Stanley Cup Finals.
They made it this far with relative ease, having swept the Kings in round one and later topping the Jets 4-1. They also struck first against the Capitals, winning game one on Monday night. Might their journey here have come a little TOO effortlessly, though?
I get the logic of Vegas being favorites for the second game and for the series as a whole, but I’m not about to overlook Washington’s chances. They outlasted a tough Lightning team to get here, and their more challenging route to the finals could mean they’re a little more battle-tested at this stage.
Given the talent and value, I’ll roll with the Capitals at +135 to tie this thing up at 1-1 on Wednesday.
The 2018 NBA Finals tips off on Thursday night, which starts off a fourth straight title series showdown between the Cavs and Dubs.
Golden State remains the far more cohesive team and are favored heavily by Vegas to win this series. I can’t knock the logic, but LeBron James is playing out of his mind, and the Cavs just came back from a 3-2 hole to get to this point.
Cleveland has nothing to lose, and if they’re going to make any noise in this series, something tells me it may need to come right away in game one. At a crazy +660 price at BetOnline, the Cavs are worth a look this week even if you’re not a believer.
It’s never easy to bet against an elite MLB team, let alone one as good as the Boston Red Sox. The Sox are currently atop the AL East at 37-17, are 7-3 over their last 10 contests, and are even a stout 18-8 at home.
So, why am I rolling with the Jays at Fenway Park? Mostly because I don’t trust Rick Porcello.
Porcello’s hard contact ways have returned in recent weeks, while he simply isn’t managing games well. The former Cy Young winner has now allowed 17 runs over his last four trips to the mound.
None of this sounds great with tonight’s game going down in the hittable Fenway Park, while Porcello hasn’t been exactly sparkling against this Jays offense (3.86 ERA) this year.
Boston is the better team and probably wins this series, but Toronto offers elite value as a rival with nothing to lose. If a potent Jays offense can tag Porcello early, they could be well on their way to getting bettors a big upset win on Tuesday.
I love targeting big underdogs in MMA fights, simply because it only takes one punch or one wrong move on the floor for a favorite to come crumbling down.
Fedor scored us an upset win a few weeks ago, and Darren Till returned even more value last week. I’ve whiffed on a few big UFC upset picks, but I like the value associated with Vinc Pichel this week.
It’s arguable that Gregor Gillespie is onto big things. The undefeated 31-year-old has used an eclectic skill-set to KO opponents or snuff them out.
This projects as a fairly even match, as both guys know how to wrestle, have punishing fists, and have proven to be very tough to beat thus far in their MMA careers.
In fact, Pichel’s lone loss so far came via KO almost six years ago. Since then, the 35-year-old menace is 4-0 and appears to be on a mission.
As the more dominant KO force, I don’t mind attacking this matchup with his +350 price and hoping he tags Gregor early.
That does it for this week’s look at some of the best upset picks the sports world has to offer. Some weeks, I’ll really push hard and look for a big number of underdogs to back, and others, I won’t force the issue.
This is one of those weeks, as the NBA and NHL season are winding down, and there are just so many viable underdogs to back.
Hopefully this week’s picks find you well and help you win big. Either way, be sure to be on the lookout for that tempting upset pick that provides value and also has the logic to potentially carry you to a big win.
Whatever you decide to do with your wagers this week, I wish you luck!
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