David Lipsky has built a long and successful professional career.
Since leaving the amateur game behind in 2011, he has won four times, with victories on the DP World Tour, the Asian Tour and the Korn Ferry Tour among the highlights of his resume.
Through the years, Lipsky has employed several caddies, including Robert Brown and Sam Haywood. However, his current looper is Darren Woolard – and with his help, his career appears to be edging closer to another milestone.
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Woolard has plenty of experience in the game, having previously caddied for the likes of Scott Piercy, Jarrod Lyle, Taylor Montgomery and KH Lee.
Indeed, Woolard was caddying for longtime friend Piercy as far back as 2009 when Lipsky was still cutting his teeth at Northwestern University.
Therefore, there’s little wonder that Lipsky has turned to Woolard as he seeks to take his career to another level.
While Lipsky has had some notable successes, one ambition he is yet to realise is a PGA Tour title.
However, by 2025, there were signs that, with Woolard’s help, he could be edging closer to achieving the feat, first with a T3 at the John Deere Classic, followed by an identical finish at the 3M Open.
Darren Woolard helped Lipsky to T3 at the 2025 John Deere Classic
(Image credit: Getty Images)
The pair continued to find success into 2026, not least at the Valspar Championship. There, Lipsky was near the top of the leaderboard into the second half of the Copperhead Course at Innisbrook tournament as the partnership continued to reap rewards.
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