Underdog Fantasy was valued at $1.225 billion in its $100M Series C funding round in early 2025, nearly tripling its previous $485 million valuation from July 2022. Notable investors in Underdog Fantasy include BlackRock, Acies Investment, Mark Cuban, and Kevin Durant.

Underdog Fantasy was founded in 2020 by Jeremy Levine, Brandon Stakenborg, and Trevor John, bringing together expertise from previous fantasy sports ventures including StarStreet and DRAFT.

Underdog found product-market fit as an innovative fantasy sports platform for sports enthusiasts seeking more engaging and less time-consuming alternatives to traditional season-long fantasy leagues. Their flagship Best Ball tournaments eliminated the need for weekly lineup management while maintaining the excitement of drafting and following players throughout a season.

The platform offers three core products: Best Ball tournaments, Pick'em contests, and a recently launched sportsbook. In Best Ball, users draft a team once before the season, with the platform automatically selecting optimal lineups each week based on player performance. Top-scoring teams advance through tournament rounds competing for substantial prize pools.

Pick'em contests allow users to predict individual player statistical performances by selecting "higher" or "lower" than projected lines. These selections can be combined into multi-leg entries similar to parlays, with all selections needing to be correct to win.

Underdog Fantasy is a fantasy sports and sports betting platform that generates revenue primarily through contest fees, taking approximately 10-15% of entry fees for fantasy contests and tournaments.

The company offers several distinct product lines. Its flagship product is Best Ball tournaments, where users draft teams at the beginning of a season with no ongoing management required. The platform automatically selects optimal lineups each week, with teams advancing through tournament rounds to compete for substantial cash prizes like the $15 million prize pool for Best Ball Mania.

Underdog's Pick'em contests allow users to predict individual player performance by selecting "Higher" or "Lower" than projected statistical lines. These can be combined into 2-5 leg entries similar to parlays, with payouts increasing with more selections. The company builds in a house advantage on these contests as a revenue stream.

In March 2024, Underdog expanded into traditional sports betting with the launch of its sportsbook in North Carolina. Unlike many competitors who use white-label solutions, Underdog built proprietary technology for its sportsbook, which offers traditional betting markets and integrates with existing fantasy accounts.

Underdog Fantasy operates in a market that includes traditional fantasy sports platforms, daily fantasy sports (DFS) operators, player prop betting sites, and full-service sportsbooks.

ESPN Fantasy and Yahoo Fantasy dominate the traditional season-long fantasy sports market with their established platforms and extensive user bases. These companies offer free-to-play leagues with optional premium features but lack the daily engagement and prize structures that Underdog specializes in.

DraftKings and FanDuel represent the largest competitors in the daily fantasy sports space, with massive user bases and marketing budgets. Both companies have expanded beyond their DFS roots into full sportsbook operations, creating comprehensive sports betting ecosystems. Unlike Underdog, these companies rely heavily on white-label technology solutions rather than proprietary platforms.

Sleeper has carved out a niche with its social-focused fantasy platform, emphasizing user engagement through in-app chat features and simplified gameplay. With significant venture funding and a rapidly growing user base, Sleeper targets a similar demographic to Underdog but focuses more on season-long engagement than daily contests.

PrizePicks stands as Underdog's most direct competitor in the player prop pick'em space. Both companies offer similar products allowing users to predict player statistical performances. PrizePicks has faced similar regulatory challenges to Underdog regarding the classification of these contests as skill games versus betting.

Monkey Knife Fight (acquired by Bally's) pioneered the player prop fantasy format but has lost market share to newer entrants like Underdog and PrizePicks. Several smaller competitors including Boom, Chalkboard, Dabble, FanUp, and ParlayPlay have entered this segment with varying degrees of success.

With its March 2024 launch in North Carolina, Underdog now competes directly with established sportsbooks including DraftKings Sportsbook, FanDuel Sportsbook, BetMGM, Caesars Sportsbook, and ESPN BET. These operators offer comprehensive betting markets across all major sports with substantial marketing budgets and established brand recognition.

The sportsbook market is characterized by high customer acquisition costs and increasingly sophisticated product offerings. Underdog's proprietary technology platform represents a potential advantage against competitors using white-label solutions, potentially enabling faster innovation and unique betting products.

The competitive landscape is further complicated by regulatory challenges, with state-by-state regulations creating a patchwork of markets with different legal requirements. This regulatory environment has led to industry consolidation, with smaller operators struggling to manage compliance costs across multiple jurisdictions.