The veteran left-hander finished T4 on debut here in 2009 and while he missed the cut in his only other appearance in 2011 will like his chances of another good result this week.
As the bulk of the PGA TOUR's big names tee up in the WGC – Dell Match Play in Texas, the opposite field Puerto Rico Open presents a big opportunity for the nine Australians in the field, Chalmers included.
Playing on limited PGA TOUR status for the season a win would secure Chalmers a card for two years while a high finish will go a long way towards securing playing rights for 2017.
Chalmers is joined in this week's field by Robert Allenby, Aaron Baddeley, Cameron Smith, Rhein Gibson, Rod Pampling, Cameron Percy, Mark Hensby and Jarrod Lyle.
Like Chalmers, Pampling has good memories of the Trump International course after a T10 finish here last year and is in need of a turnaround in form after a difficult start to his season.
Having won his PGA TOUR card via the 2015 Web.com Tour money list, Pampling has found the going tough early in the year with just one cut made in five starts.
Rhein Gibson is in a similar position after also graduating from the secondary Tour, three cuts from nine starts not the debut he was looking for on the world's biggest circuit.
The story is similar for Jarrod Lyle and Cameron Percy in 2016, Lyle missing five of six cuts including his last four in a row while Percy has played two weekends from four starts.
For Cameron Smith a rough start to his PGA TOUR career seems in the rear view mirror with improved showings in recent weeks and with his Masters debut just a fortnight away he will be motivated to play well.
Smith has made the cut in each of his last three events on some difficult golf courses suggesting his game is in good shape and it would be no surprise to see him contend this week.
Headlines at a glance
- World Cup of Golf hospitality now on sale 25.05.2016
- Golf Trader - PGA Member David Fearns (Jnr) 25.05.2016
- Big Aussie assault at second Senior Major 25.05.2016
- McCardle, Wood to build on good China start 25.05.2016
- Strong Aussie contingent at Czech Challenge 25.05.2016
- Scrivener reaps rewards with Wentworth start 25.05.2016
Big Aussie assault at second Senior Major
Four Australians will be in the field for the year's second senior major which tees off this week in Michigan.
PGA Tour China
McCardle, Wood to build on good China start
After making good starts in the first event of the season to be in the top-10 on the PGA TOUR China Order of Merit, Max McCardle and Chris Wood will b...