Bob Gilder, Butch Sheehan, Dick Mast and Jerry McGee share fourth place at 3-under-par 69. Joe Inman and Pat McDonald are one stroke further back at minus-2.
Jan Stephenson, a member of the LPGA Tour playing on a sponsor's exemption, struggled to an 8-over-par 80.
Irwin, the three-time defending champion, is looking to become the first player in Champions Tour history to win the same event four straight years. With his win here back in 1997, he joins Jack Nicklaus as the only players to win the same tournament on four occasions.
Irwin got rolling on the Palmer Course at the Turtle Bay Resort with a 10-foot birdie putt on the second. A poor drive off the sixth tee led to a bogey, but he responded in fine fashion.
He dropped a sand-wedge within 10 feet for birdie at the seventh and came back with a 12-foot birdie putt at the eighth. He made it three straight with a tap-in birdie on No. 9.
Irwin, the Champions Tour's all-time leader in wins, rolled in a six-footer for birdie on the 14th to move to 4-under. Thanks to a pair of nice pars saves, he managed to maintain a share of the lead.
'One of the better days as far as my back goes,' said Irwin, who has battled back problems all summer. 'I feel comfortable on this course and I've had a lot of success here. You just have to try to not overpower the wind.'
Quigley meanwhile burst out of the gate with three straight birdies from the first. He made nice par saves on the fourth and eighth before birdieing the ninth.
On the back side, he knocked a 7-iron to 20 feet to setup birdie at the 11th. He came right back with a four-foot birdie putt at the 12th to get to get to 6-under.
The 56-year-old three-putted for bogey on the par-3 13th and dropped another stroke at the 17th to fall back into a share of the lead.
'Hawaii has been very good for me,' said Quigley. 'I hit the ball low and with this wind it plays right into my game. If I can play with Hale today, tomorrow and Sunday, I'll have a chance to win.'
Caldwell mixed a birdie and a bogey over his opening nine holes. Around the turn, he birdie three of the first five holes, but dropped another stroke at the 15th. He climbed into a share of the lead with back-to-back birdies from the 17th.
Stephenson, who came under fire Friday for published remarks that quote her as saying foreign players are 'killing' the LPGA Tour, is tied for 74th place. She became the fifth women this year to play in a men's event joining Annika Sorenstam (PGA Tour - Colonial), Suzy Whaley (PGA Tour - Greater Hartford Open), Michelle Wie, who played in events on the Nationwide and Canadian Tours and Laura Davies (Asian PGA Tour - Korean Open).
Stephenson bogeyed three of the first four holes before dropping shots at the sixth and ninth to make the turn at 5-over. She then dropped shots on three straight holes from the 10th. She did manage to card a birdie on the 15th, but bogeyed the very next hole to finish at 8-over.
Hugh Baiocchi, Allen Doyle, D.A. Weibring, Tom Kite, Bobby Lincoln and Tom Purtzer are the final players under par as they stand at 1-under-par 71 in a tie for 10th.