Baltimore Couple Wins Second Big Lottery Prize in Two Years, With Same Numbers

BALTIMORE — Lightning struck twice for longtime Maryland Lottery player Paul Cypress, who has claimed his second $50,000 Pick 5 prize in as many years, using the exact same set of lucky numbers. The Baltimore resident, who has been a loyal Lottery player for more than 35 years, discovered his latest win during a Christmas party after his wife reminded him to check his tickets. He kept the news quiet until returning home, where he and his wife celebrated the remarkable repeat victory privately. Paul’s lottery journey began decades ago when a family member gifted him a winning scratch-off ticket, sparking his enthusiasm for the games. While he regularly plays Pick 4 and scratch-offs, Pick 5 remains his favorite—and most lucrative—game. Reflecting on his win, Paul said he plans to set aside his winnings for his children’s future and save the rest, while affirming his commitment to keep playing. “Absolutely, most definitely want to keep playing,” he told Maryland Lottery officials. The retailer that sold the winning ticket, Jessup Shell on Annapolis Road in Hanover, will also receive a $500 bonus from the Lottery.