streak for the cash prizes

ESPN – September 2019 Streak for the Cash Challenge (Expired)

$35,000 in Cash Prizes Will Be Awarded

Note: This sweepstakes has expired, but you can find many sweepstakes with similar prizes on the Cash Sweepstakes List.


Do you have a good nose for how sporting events will turn out? Guess the outcomes of various sporting challenges, like which team will win a match or whether points will be scored in a particular part of the game, and you could win cash prizes worth up to $25,000 from ESPN’s September 2019 Streak for the Cash Challenge. This sweepstakes has expired.

Sweepstakes Links:

  • Sweepstakes Entry Form:
  • Sweepstakes Rules:
  • Sweepstakes Homepage:



Residents of the United States, the United Kingdom, Singapore, and Canada (void in Quebec), 18+ and above the age of majority

Start Date:

September 01, 2019

End Date:

September 30, 2019 at 11:59 p.m. ET

Entry Frequency:

1 x daily per person/email

Sweepstakes Prizes:

Longest Streak Monthly Prize: $25,000 in cash. (ARV: $25,000)

Most Wins Monthly Prize: $5,000 cash. (ARV: $5,000)

Beat the Expert Monthly Prizes (5): $1,000 cash. (ARV: $1,000)

Additional Comments:

You must be a member of or one of their affiliated sites to enter. Membership is free and available online.

To enter, guess the outcomes of various sporting events. For example, you may guess that a certain number of goals will be scored during a soccer game, or that one team or another will win a hockey match, or that one basketball player will score more points than another.

The person who has the longest winning streak will win the grand prize.

ESPN will select an “expert” to play along this month. One person with a longer streak than the expert will be randomly chosen to receive the Beat the Expert prize.

The person who selects the most wins each month, even if they’re not in a row, will receive the “Most Wins” prize.

Note that if you enter through the mobile app, be sure to update the app to see the new monthly prizes.

Enter ESPN's September 2019 Streak for the Cash Challenge for your chance to win cash prizes worth up to $25,000. The giveaway ends on 9/30/19. This sweepstakes has expired.

Your Web Browser is no longer supported

To experience everything that has to offer, we recommend that you upgrade to a newer version of your web browser. Click the upgrade button to the right or learn more.

  • Make Pick
  • Leaderboards
  • Winners
  • My Groups


Monthly Grand Prize – One (1) Prize (November 2020):

The entrant who accumulates the longest winning streak during the month-long Challenge Period will be considered the Grand Prize winner. The winner will be announced on the first day of the next month. Monthly Grand Prize winner will win US $3,000.

Monthly Prize – One (1) Prize (November 2020):

The Challenge will also have a monthly wins portion. A “most wins” prize will be awarded to the entrant who accumulates the MOST WINS during the month-long Challenge Period. The Most Wins Monthly Prize will be announced the first day of each sequential month and will be awarded US $1,000.

Beat the Expert Prize – Five (5) Prizes (November 2020):

The Challenge will also have a new Beat the Expert contest. During the Challenge Period (month), a designated “Expert” will make picks. If your longest streak beats the Expert’s longest streak, you will entered into a random drawing at the end of the month. Five (5) winners will be drawn, and each will win US $200.

Play Streak to build the longest streak of correct picks from a daily list of professional and college sports matchups and win cash prizes each month!