David Lipsky is slowly finding his pace on the PGA Tour. It took him a while to get there, but he has been a frequent flyer in the big leagues since the 2021-22 season. Over the years, the 37-year-old has also come close to grabbing his first win on the Tour recently. And he will give his caddie, Darren Woolard, a lot of credit for that.

Ever since 2025, Woolard’s presence has immensely helped Lipsky perform better. He got a few great top-5 finishes last season thanks to his looper. The PGA Tour pro finished at T3 in the 3M Open and the John Deere Classic last year. They also got a T4 in the Zurich Classic in New Orleans together.

It’s not like Lipsky has not won anything so far. He has three titles to his name from the European Tour. However, the 37-year-old won all of them by 2018. So Woolard wasn’t around to celebrate with him back then.

Speaking of Lipsky’s team, he has changed quite a few caddies over the years. He has previously worked with Robert Brown and Sam Haywood. However, things seem to be working out with Woolard as they are enjoying their second season together. The Las Vegas local has also been far more consistent along with his current bagman. He had no third-place finishes in his career before Woolard joined his team last season. Now he has two!

Coming to Woolard and his experience in the field, he has worked with a number of top pros. He used to carry the bags for Scott Piercy, Jarrod Lyle, Taylor Montgomery, and K.H. Lee.

Interestingly, Woolard has also changed his bosses frequently over the last few years.

David Lipsky’s short stints with his former bosses

Looking at how well they are getting along, David Lipsky and Darren Woolard are certainly compatible with each other. That might be a rare situation for the bagman, as he has shuffled around with various bosses in the last few years.

In 2023, Woolard worked with Taylor Montgomery. They nearly won the Fortinet Championship together after finishing solo third in the event. However, things didn’t seem to work out between them as the looper changed his boss not long after.

K.H. Lee brought in Woolard to carry his clubs in 2024. A 2-time AT&T Byron Nelson champion, Lee didn’t have a great season with Lipsky’s current caddie carrying his bag. He barely managed to finish in the top-5 twice.

Finally, Woolard and Lipsky joined forces, and they have been working well since. The 37-year-old is consistently progressing on the fairway. The veteran caddie also seems to be getting along with his boss this time around. Getting closer to winning his first PGA Tour title, Lipsky will be eager to stick with Woolard if they finally see the former winning.