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It's not looking good for Doug Polk's chances of winning an online poker challenge on ClubWPT Gold after a costly Saturday session that saw "Code Doug" go from up $20,000 to well in the red.

The Upswing Poker founder sought to win $100,000 in one month on the new sweepstakes poker site. But as the midway point approaches, he's now further behind his goal than when the challenge began.

Polk started off the challenge playing low-stakes heads-up games, and fell behind a few thousand bucks early. He stepped up to mid-stakes and things turned around for him in the positive direction. But that all came to an abrupt halt on Day 12.

Rough Day for Texas Poker Room Owner

Polk livestreamed for six hours on Saturday, and he ran into a nemesis who plays under the screenname "IamBenough." The two played $10/$20 heads-up no-limit hold'em on ClubWPT Gold for hours, and it turned out to be a bloodbath.

The brutality began about 30 minutes in on a board of 5♠10♦J♣3♠Q♠. Polk had J♠2♠for the third nuts. He checked the river to set the trap before check-jamming all in for nearly $4,000 and received a snap-call from A♠6♠, the nut flush. His opponent took down an $8,000 pot, one of many coolers to come.

Polk did bounce back within the hour when he turned trips to crack top pair for a $6,500 pot. But the co-owner of Texas' The Lodge Card Club continually ran into it against "IamBenough" from there on out.

https://twitter.com/DougPolkVids/status/1901024822055858366

In one hand, "IamBenough" four-bet from the button with 9♣8♣against Polk's A♦J♦. The flop came out 8♦9♦9♥, and little did Polk know he was drawing dead despite having the nut flush draw, which he'd hit when the 5♦appeared on the turn. All the money went in on the river, and the challenge host's opponent took down another $8,000 pot.

The match would continue for quite some time, but it was a lopsided affair. "IamBenough" ended up wrecking Polk for nearly $35,000, over 1,700 big blinds. Polk would find a new opponent to face over the final hour of his livestream on YouTube and Twitch, and he'd drop another $2,000 or so before calling it quits for the day.

Polk, who entered the session $20,160 in the black, lost $36,480 on Day 12, bringing his combined tally to a net loss of $16,320. He's now $116,320 away from reaching his one-month goal on ClubWPT Gold, a social poker site he serves as an affiliate for but heavily critiques. To hit the $100,000-in-a-month goal, he'll need to average winning approximately $6,400 per day the rest of the way.

The three-time World Series of Poker (WSOP) bracelet winner has vowed to give away all his winnings to those who sign-up for ClubWPT Gold and use the code "Code Doug." But even if he loses, he'll still give out $100,000. He'll be back at it on Monday following a day off on the poker site he's offered up his harsh but honest review of in a YouTube video.

ClubWPT Gold's X account has been having some fun at Polk's expense during the challenge, and on Saturday, they tweeted at the poker pro: "You didn't have to give all $100k away in one day." Perhaps, they'd cool the trash talk if Polk stopped cracking on the site and the "vlog watchers" who play on ClubWPT Gold.

The challenge isn't over, however. He isn't ready to throw in the towel just yet and could still get the last laugh.