At stake were exemptions into four Nationwide Tour events in 2005, as well as $10,000 cash and a sleek new Ford 500.
Even though we both wanted to kick each other's heads in, we still had a lot of respect for each other, said 35-year-old Donatello about the match up.
'I was not feeling any confidence at all standing there,' added Henley about starting off the match.
Shaking off first tee jitters, both players striped their opening tee shots down the fairway to get the match underway. Both made routine pars on the par-4 first hole before moving on to the par-5 second.
A wayward shot from a greenside bunker that flew the green cost Donatello dearly, as Henley was able to win the hole with a par and draw first blood.
Both players then halved the next two holes before arriving at the par-4 fifth. Henleys tee shot found a fairway bunker and then he added to his troubles when his resulting approach never left the sand. Donatello rolled in his par putt to even the match at all square.
A miraculous save at the par-3 sixth from Henley was all for naught, as Donatello center cut his birdie putt to go 1-up. Both players proceeded to birdie the par-5 seventh and then Donatello made a big statement by rolling home a 15-footer on the par-4 eighth for his third birdie in a row and a solid 2-up advantage.
Henley came right back however at the par-3 ninth, nearly holing his tee shot en route to a birdie to cut Donatellos lead to just 1-up.
The players halved the next three holes and came to the par-4 12th where a little controversy was sparked by a ruling involving Donatello getting relief from a sprinkler head on the fringe of the green.
Henley shook off the matter by draining a birdie putt to get the match back to all square, then missed an opportunity to go 1-up when he just missed a birdie try on the following hole.
'That was the most angry I have ever been on a golf course,' said Donatello in frustration after some sloppy play. 'It was really poor that I handled myself like that but it just tells you how important one shot could make the difference between winning and losing.'
The match seesawed over the next two holes with Henley winning the 14th with a simple par and Donatello fighting back at the 15th with a wonderful up-and-down for birdie to even the match once again.
With three holes to play and the match all square, Henley blew a golden chance to seize control when he left his birdie effort dead in the heart but just an inch short. They both made pars on the par-4 17th and then headed to the 18th to try and decide who would become the winner of the Big Break II.
After both players hit quality tee shots, Donatello stuck his approach 20 feet from the flag and then watched as Henley uncharacteristically 'chilly chunked' his attempt into the front bunker.
With Donatello almost assured of a two-putt par, Henley needed a miracle up-and-down to stay alive. With lady luck apparently on his side, Henley lofted his sand shot to within several feet and knocked in the putt to stave off elimination.
It was on to sudden death and Henley could all but taste victory on the first extra hole but watched in horror as his birdie effort came agonizingly close, coming to rest hanging over the edge of the cup.
On the second playoff hole, Donatello hit the par-5 green in two but was well short of the flag. Henley's approach, meanwhile, nestled up to within 10 feet of the pin and he was looking at an eagle for the win.
Donatello's long lag putt came to rest 6 feet short of the cup and he dodged a bullet when Henley's eagle effort burned the edge of the cup.
As Henley tapped in for birdie, Donatello sized up his putt that would extend the match. His effort had the line but unfortunately didn't have enough speed as the ball stopped just inches from the cup giving Henley the hard fought win.
'I just stepped over a huge hurdle in my golf career.' said the visably emotional Helney. 'An old caddie friend told me a long time ago, 'Kippie old boy, just keep walking up that mountain, the sun will be shining.'
'I can now see the sun.'
'This is hard to swallow even though a good guy won,' said a very disappointed Donatello. 'I honestly thought this was my last straw. I'm going to try to keep my head held high and be proud of myself and to think I came out of here a winner, even though, I didn't get all the great things that Kip got.'