Who Is David Lipsky's Caddie?

David Lipsky and Darren Woolard at the Valspar Championship — David Lipsky currently has Darren Woolard on his bag

(Image credit: Getty Images)

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.

Article continues below

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.

Caddie Darren Woolard and David Lipsky — Darren Woolard helped Lipsky to T3 at the 2025 John Deere Classic

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.

Mike has over 25 years of experience in journalism, including writing on a range of sports throughout that time, such as golf, football and cricket. Now a freelance staff writer for Golf Monthly, he is dedicated to covering the game's most newsworthy stories.

He has written hundreds of articles on the game, from features offering insights into how members of the public can play some of the world's most revered courses, to breaking news stories affecting everything from the PGA Tour and LIV Golf to developmental Tours and the amateur game.

Mike grew up in East Yorkshire and began his career in journalism in 1997. He then moved to London in 2003 as his career flourished, and nowadays resides in New Brunswick, Canada, where he and his wife raise their young family less than a mile from his local course.

Kevin Cook’s acclaimed 2007 biography, Tommy’s Honour, about golf’s founding father and son, remains one of his all-time favourite sports books.

You must confirm your public display name before commenting

Please logout and then login again, you will then be prompted to enter your display name.