March Madness First Round Upset Parlay: Targeting VCU, High Point in Round of 64 Long Shot

March Madness is finally set for opening tip-off on Thursday and Friday, offering 32 highly anticipated First Round matchups to watch during the 2025 NCAA Tournament. We're looking for upsets galore in the First Round. Four underdogs stand out and hold enough value to parlay into a huge payday.

NCAAM handicapper Matt MacKay has constructed a First Round Upset parlay to bet during March Madness using the latest odds available on Sportsbook at bet365. Matt's got analysis to back up every pick and why these underdogs have a chance to win outright on Thursday and Friday.

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March Madness First Round Upset Parlay (+26411)

No. 14 Montana (+1000) vs. Wisconsin

Montana may be a 14 seed but their ranked 65th in offensive rating this season. The Grizzlies just won the Big Sky conference and went 15-3 in conference play, going 14-1 SU in their last 15 games played.

Wisconsin has a lot of talent but the Badgers live and die by their three-point shots. We saw this backfire against Michigan during the Big Ten Tournament Final. If their shooters go cold, it's going to be difficult to keep up with Montana's scorers.

This line has already moved from 11-1 to 10-1 in favor of the Grizzlies to win outright and upset Wisconsin on Thursday afternoon. Let's go big and back Montana to pull off a huge upset over John Tonje and the Badgers in the First Round.

No. 11 VCU (+115) vs. BYU

Virginia Commonwealth (VCU) has also seen its odds shorten ahead of a First Round matchup against 6th-seeded BYU. The Rams won the A10 with a 28-6 record, playing sound defense, ranked eighth in the nation for points allowed per game (62.4) this season.

BYU is a high-volume three-point shooting team, which is a big reason why the Cougars have a 117.3 offensive rating (16th) and score 81 points per game. VCU's offense isn't a slouch, scoring 77.1 points per game this season, while ranked 34th with a 115.2 offensive rating.

The 11th-seeded Rams are led by their back-court tandem of Max Shulga and Joseph Bamisile, each averaging over 15 points and five rebounds per game for VCU. Despite all of the success BYU's had in 2025, I think VCU's defense will contain the Cougars' explosive offense, which will allow them to win this game.

No. 10 Utah State (+195) vs. UCLA

Utah State is a 10-seed going up against 7-seed UCLA in the Midwest Region. The Aggies rank ninth in offensive rating (119.8) and average over 80 points per game on offense this season.

Their defense is a bit of a weakness, ranked 151st with a 103.7 defensive rating. However, UCLA's offense has faltered significantly down the stretch this season. The Bruins are 112th in offensive rating (112.4) and specialize in playing defense. Yet they were routed by Wisconsin's three-point shooting in the Big Ten Tournament.

Utah State is a team that can get hot and score buckets in bunches. They'll have a top-ten offense ready to roll against UCLA and will test the Bruins' defensive capability.

Ultimately, I believe the Mountain West team with the better offense beats the Big Ten team with a better defense in this matchup.

No. 13 High Point (+280) vs. Purdue

High Point is one of the most popular underdogs being bet on during the First Round of March Madness. Despite the popularity, I believe this is a quality pick. The Panthers rank second in the nation for offensive rating (121.7) and draw a matchup against 4-seed Purdue, who struggles to defend.

The Boilermakers rank 241st in defensive rating (106.8) and lack depth on offense. Most of their scoring comes from F Trey Kaufman-Renn and G Braden Smith, combining for 36.3 points per game.

High Point's offense is red-hot and they just breezed through the Big South conference tournament. They haven't lost since January 16th, winning 14 consecutive games ahead of their First Round tilt against Purdue.

The Panthers' red-hot shooting will exploit Purdue's defense. Yes, Purdue is a top-20 team in offensive rating, yet High Point ranks 98th in defensive rating, significantly better than the Boilermakers' porous defending.

Let's back High Point to win their biggest game of the season and upset Purdue as a 13-seed in the Midwest Region on Thursday afternoon.

March Madness First Round Upset Parlay (+26411) (Bet $10 to Collect $2,651.10)

• Montana (+1000)
• VCU (+115)
• Utah State (+195)
• High Point (+280)