David Lipsky has spent this season chasing one thing his résumé still lacks: a PGA Tour title. He came within a single shot of it at the Valspar Championship in March with Darren Woolard, a veteran caddie who has been around the game since before Lipsky turned pro. Their pairing looked like a steady one, so it came as a surprise when the two reportedly reached a breaking point in Japan.
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Golfweek’s Adam Schupak reported that Woolard had simply had enough. According to the report, he essentially told Lipsky to find someone else to carry the bag for Sunday’s final round. However, neither man had publicly addressed the situation in reports available at the time of writing.
The decision came at the Baycurrent Classic at Yokohama Country Club, which ran from October 8 to 11. As a no-cut event, it meant Lipsky would play all four rounds.
Notably, the split came after a frustrating week. Lipsky opened with a 66 on Thursday but slipped to 72 and 73 in the following rounds. Moreover, his Saturday ended with bogeys on two of his last three holes. Sunday looked even worse as he bogeyed four of his first five holes but recovered to shoot a one-under 70, finishing tied for 54th at three under.
While this week was harsh, Woolard had also helped Lipsky put together some of his best results. Lipsky tied for third at both the 2025 John Deere Classic and the 3M Open, with his caddie by his side on both occasions. His best result came at the Valspar Championship, where he finished one shot behind Matt Fitzpatrick at 10 under. The runner-up finish earned him $991,900 and 300 FedEx Cup points. Moreover, the performance likely helped him secure conditional status for signature events after the Masters.
That said, their partnership did not last long. Woolard began caddying for Lipsky at the 2025 John Deere Classic, with their best result coming at the Valspar Championship.
Amid all this, a win on the PGA Tour remains the missing piece. Lipsky turned professional in 2011 after attending Northwestern and won the 2012 Handa Faldo Cambodian Classic in a playoff. He then added the 2014 Omega European Masters and the 2018 Alfred Dunhill Championship to his résumé. Notably, none of those victories came on the PGA Tour. Sky Sports also noted that he was winless in 104 events when he led the 2024 Procore Championship after the first round. That week, too, ended in a runner-up finish, five shots behind Patton Kizzire.
Ultimately, what prompted the pair to end their partnership remains unclear, and reports have not established whether the split is permanent. Schupak reported that a Tour official confirmed Lipsky began the final round with a different caddie.