Olazabal was locked in a duel with Greg Norman on the back nine of the 1999 Masters when he pulled away, only to discover that Love was making a late charge with a bogey-free back nine that featured a chip-in from 25 feet behind the green on the par-3 16th. Olazabal pulled away, however, and won by two shots.
The next year after the Champions Dinner at Augusta National, Olazabal noticed there were a few extra bottles of wine.
He had them sent to Love.
"He felt like he had beaten me from the year before, and I should have gotten something out of it," Love said.
Love made his Ryder Cup debut in 1993 at The Belfry, teaming with Tom Kite against Seve Ballesteros and Olazabal, the most successful partnership in the history of the matches. The Americans handed the "Spanish Armada" one of only two defeats in their Ryder Cup career. Just his luck, Love had to face them twice more, both losses.
"Kite and Seve were bashing away, and we were on the side trying to be friendly," Love said. "We always had that respect for each other. There's a lot of connections. I was very pleased when I found out he was going to be the captain."
Of all the details that go on behind the scenes in what Love refers to as a "very structured" event, he said there has never been "one problem, one controversy."
"It speaks to what kind of guy he is," Love said.
One of the discussions was about clothing. The Americans wear a collection of red, white and blue, though it doesn't have full ownership of those colours. All indications are that the U.S. team will have red shirts for Sunday, presumably so that it won't clash with European blue.
Olazabal is said to want blue for Sunday as a tribute to what Ballesteros typically wore in the final round. Ballesteros died in May 2011, making this the first Ryder Cup without the great Spaniard who was so responsible in reviving the matches.
"He was very understanding of it, and I'll say no more at the moment," Olazabal said of the team colours and conversations with Love.
Make no mistake, though. Both teams are desperate to hold that 17-inch gold trophy that Olazabal brought over on the plane from London. Europe has won six of the past eight times in the Ryder Cup, including a 14 1/2-13 1/2 win in Wales two years ago.
Tiger Woods said last week that captains take on the personality they showed as players, and Love would be quick to agree with that, especially when it comes to Olazabal, a two-time Masters champion who fought through injuries.
"You know he's competitive, and it's going to be competitive," Love said. "But it's organized, friendly, cordial, respectful. That's how it should be."
Indeed, this is a different Ryder Cup from when both captains first played.
That much was clear by the manner in which the European team arrived. Olazabal stepped off the plane at an airport in Rockford, about 45 minutes from Medinah, with the Ryder Cup trophy in his possession. He was followed off the plane by only three of his 12 players -- Francesco Molinari, Paul Lawrie and Nicolas Colsaerts.
Everyone else was already here.
Rory McIlroy and Lee Westwood, among four players who were in Atlanta on Sunday for the Tour Championship, are moving to south Florida. Luke Donald lives about 45 minutes away on the north side of Chicago.
It wasn't that long ago that Team Europe came over together because that's where so many lived and played -- Howard Clark and David Gilford, Sam Torrance and Mark James, Ian Woosnam and Colin Montgomerie.
Olazabal didn't see that as a problem.
"Obviously, when you look at some of the European players, they have their home base here," he said. "They play the tour over here. They are very familiar with the golf courses around here, with their opponents, and in that regard, I think they feel really more comfortable with the whole situation of coming here to the States to play The Ryder Cup. It has changed in that respect, and also that they have realized through the years that they have been able to compete against the players here.
"And that somehow boosts your confidence, and that is a very important part when you are playing match play."
Still, there was a certain charm about having the team arrive as one.
Love remembers his first Ryder Cup in 1993, when U.S. captain Tom Watson assembled his group in New York and spoke of a grand adventure to Europe with the sole purpose of bringing back the cup.
Golf is different now.
"I miss that a little bit," Love said. "We all gather and fly over. They fly over here. That was a really cool thing. But I think what we have got now is a much bigger event."
Noting that so many of the world's best players are at Medinah Country Club, Love said that golf has become "incredibly better."
"What we have in our team rooms now and the camaraderie between the two teams is just incredible, and it's amazing how much it's changed over the years," Love said. "And we're playing against our friends, but it's still as intense -- maybe even more -- because we are more familiar with them.
"That doesn't make it any less competitive," he said. "It just makes it that we know each other a lot better. Makes the team room party on Sunday night a lot more fun."