On April 7, 2019, Conners won the PGA Tour's Valero Texas Open by two strokes over Charley Hoffman, earning the final place in the 2019 Masters Tournament. Due to his conditional status, Conners had to play in a Monday qualifying event, where he earned the final spot after a six-man playoff. He became the first Monday qualifier to win on the PGA Tour since Arjun Atwal at the 2010 Wyndham Championship. The first place prize was $1,350,000. Conners finished the 2019 regular season in 31st place. He finished 21st at The Northern Trust and 7th at the BMW Championship, which earned him a spot at the Tour Championship.