The 59-year-old, who was pipped by Colin Montgomerie in a play-off in the Travis Perkins Masters at Woburn just under a year ago, signed for seven birdies as he carded a season’s best 66.
“I took my chances and putted well,” said Drummond who partnered 1991 Masters winner Ian Woosnam, and two-time Senior major champion Roger Chapman.
“It was nice to have that draw,” he added. “I had to look twice at the starting sheet when I saw who I was playing with.
“They are good players, very solid, and I’ve got no complaints with anything today.”
Fellow Scor Gordon Brand Jnr opened with a 67, as did Gordon Manson, who hails from Scotland but now plays under the Austrian flag.
Colin Montgomerie made a poor start in the Boeing Classic to find himself 12 shots off the lead in the Champions Tour event in Seattle.
On a day when American duo Kirk Triplett and Gene Sauers set the pace with matching 65s, the Scot crashed to a 77 that contained six bogeys.
It left the three-time Senior major winner sitting joint-74th in a 79-man field.
Senior Open champion Paul Broadhurst also struggled to a 74.
Catriona Matthew is lying nine shots off the lead at halfway in the Canadian Pacific Women’s Open in Calgary.
She followed an opening 69 with a 72 for a three-under total as Thai player Ariya Jutanugarn raced three shots clear of the following with rounds 68 and 64.
Northern Ireland’s Stephanie Meadow is lying joint-second after opening efforts of 66 and 69.
Clydebank and District’s John Henry claimed his best finish of the season on the PGA EuroPro Tour by claiming a share of fifth spot in the FORE Business Championship at The Oxfordshire.
He signed off with a 72 for an eight-under 208 total as Welshman Mark Laskey claimed the £10,000 top prize on 200 following last-round 65.
Not a single Scottish player survived the cut in the Bridgestone Challenge at Heythrop Park, where Belgian Thomas Detry kept up his red hot form.
Detry followed his first-day 60 with a 67 to sit on 17-under, leading by four shots from South African Thriston Lawrence.
Bob Cameron and his amateur partner Gordon Hedley ensured lightning of the metaphorical kind did not strike thrice at Gleneagles by winning the PGA Super 60s Championship.
In doing so, the pair prevented defending champion Murray White from recording an unprecedented hat-trick of victories in the tournament for PGA Professionals and their amateur sidekicks aged 60 or over.