He finished the Champions Tour's third major with a winning score 4-under-par 284 in just his second trip to the Senior British Open. This was his 18th appearance in a major championship overall.
'I'm still trying to rationalize at the moment,' said Oakley, whose best previous finish in a major was a tie for 29th at the 2003 U.S. Senior Open. 'I'm not used to all of this attention, but it certainly is rewarding and I'm very much excited and looking forward to what's going to happen to me the next year, actually.'
Oakley, who is the director of golf at the Rookery in Delaware, was the winner at the 1999 American PGA Senior Club Professional Championship. He earned $295,212 for this win and also gains a spot in next week's U.S. Senior Open.
Eduardo Romero, who recently turned 50, put together a remarkable run of golf over the final 10 holes, but he fell just short. Romero carded six birdies in that span to close a round of 5-under 67, the best round of the tournament.
Romero shared second place at 3-under-par 285 with Tom Kite. Romero carded two of the tournaments 13 rounds in the 60's, but was done in by scores of 75-74 in the middle two rounds. Kite closed with a 3-under 69.
Oakley seemed unfazed to open his round. He birdied the par-5 second for the fourth time this week. However, things took a turn for the worse from there at Royal Portrush Golf Club.
The 55-year-old bogeyed the fourth and fifth to fall behind Ford Senior Players Championship winner Mark James. James then fell of the pace with a pair of bogeys of his own, and the lead fell to Don Pooley and Kite.
Kite, who had eagled the second, birdied the ninth and 10th to jump to minus-4 and two strokes clear of the field. Oakley moved back to 2 under with a birdie at the seventh, but he then bogeyed the eighth.
Kite, who won one major on both the PGA Tour and the Champions Tour, began to struggle on the back nine. He bogeyed the 12th and 14th to slide back to minus-2.
Meanwhile, Oakley took control of the tournament. After his bogey at the eighth, Oakley rolled in a birdie at the ninth. He came right back to birdie the 10th.
Oakley climbed back into the lead at minus-4 with a birdie at the par-3 11th. He was not done there either. Oakley moved to 5 under as he birdied the par-3 14th.
Oakley fell back to 4 under with a bogey at the 16th, while Romero and Kite fought back into contention.
Romero spread two bogeys and two birdies over his opening eight holes to remain at plus-2. He started his climb up the leaderboard with three straight birdies from the ninth.
The Argentine slipped back to even par overall with a bogey at the par-4 13th, a hole which he played at plus-3 for the week. Romero kept battling though.
He rolled in three consecutive birdies from the 15th to get within one shot of Oakley. Kite, meanwhile, rolled in a birdie at the 17h to also get to minus-3.
Romero and Kite trailed by one standing on the 18th tee. Unfortunately for them, each man only managed pars to remain at minus-3.
'I played really well today,' said Kite. 'I got real aggressive on a first putt on No. 14, which I thought I could make and I zipped it right on by. I missed the one coming back to make bogey. That hurt me, but other than that and a bad swing on 13, I played a very, very good round of golf.'
In the meantime, Oakley parred the 17th as his competitors finished out at the last. He then calmly got up-and-down from a greenside bunker for par at the 72nd hole to earn the first major championship win of his career.
'Until I got in the bunker and couldn't see the flag from the bunker, I didn't think it was that difficult a shot,' Oakley said. 'When I stood there, I saw about a 9-foot wall in front of me and I could not see the flag.
'I wanted to make sure I got it out of the bunker. I knew it would come out. I was confident it would come out. I was able to hit the shot I thought I was going to hit, but it went farther past the hole than I was hoping. I've been putting the ball very well also, and just let what happened the entire week happen again. I rode it right in and won.'
James ended the tournament with a 2-under 70 to finish alone in fourth place at 2-under-par 286. Mark McNulty and Pooley carded matching rounds of even-par 72 to finish one stroke further back at minus-1.
Bill Longmuir finished alone in seventh place at 2-over-par 290, while Carl Mason posted a 3-under 69 in the final round to finish at plus-3.
Tom Watson, the 2003 champion, shot three straight rounds of 2-over 74 to finish in a tie for 22nd at 9-over-par 297.