France's Gregory Bourdy denied David Howell what would have been an amazing victory, winning the Estoril Open de Portugal at the third hole of a play-off at Oitavos Dunes.
The Ryder Cup star, so down in the dumps about his game just two weeks ago that he changed coaches, produced a closing 64 that was his lowest round for over two years, but found it was not quite enough.
Scot Alastair Forsyth, seeking a second win in three weeks, had also tied on the 18 under par mark of 266 after two closing birdies, but fell out of the race after driving into a bush on the second hole of sudden death.
Howell and Bourdy, who stayed alive with a 12-foot putt there, then switched from the 18th to the 17th and the Swindon golfer missed the green and failed to get up and down.
It was the fifth week in a row on the European Tour that there had been a play-off. It was also the fourth time out of four Howell had lost a play-off.
Bourdy had led by four at the start of the day but a front nine of 39 left him playing catch-up.
"It was so difficult in the first nine holes. I was plus three and I lost a little bit of my game but at the start of the day I thought I had to play under par and I would have a big chance to win," said Bourdy.
"I was concentrating on my game after nine holes and I made a few birdies and I felt if I made three or four I would have a big chance.
"I did not want to see the leaderboard so I was focused on my game after nine. I thought maybe minus four or five on the back nine would be okay."
Bourdy added: "I was quite nervous at the start of the day. It was difficult because it was the first time I have been in this position and I won.
"I am so happy to win."
Howell, a member of the world's top 10 after wins over Tiger Woods in Shanghai and then in the BMW PGA Championship at Wentworth, had crashed to 247th in the rankings entering the event.
He never had a single top 20 finish all last season, falling from third on the Order of Merit to 142nd.
Bourdy, the second successive French winner after Thomas Levet's success in Spain last Sunday, had been four clear overnight and that became five when Forsyth bogeyed the first.
Yet by the seventh tee the Bordeaux golfer had not just let that advantage go, he was two behind. While he bogeyed the second, third and sixth Tunnicliff birdied them all and added another on the next.
South African Charl Schwartzel and Spaniard Gonzalo Fernandez-Castano had a taste of sharing the lead as well, but then attention turned to Howell, Bourdy and ultimately Forsyth.
Howell, out-scoring 18-year-old playing partner Rory McIlroy by seven, birdied the 16th and 17th to be ahead on his own for the first time.
The 474-yard last is where Barry Lane took a nine when leading three years ago and Howell was in danger of messing it up too when he pulled his approach and it headed for an area of scrub.
However, a thin spectator pole got in the way, it rebounded into a much better lie and with a chip to 18 inches he saved par to set the target.
Bourdy, after a front nine 39 that matched the worst of the day, came home in 31, drawing level with a fourth birdie in seven holes at the long 16th.
Forsyth looked set for a near-miss with two to play, but followed a 15-foot birdie putt on the 17th with a 25-footer at the last which curled round the back of the cup, hesitated and then was pulled down by gravity.
At the first extra hole they all parred, Forsyth missing a chance to win from 25 feet from the same line as 15 minutes earlier.
Forsyth, whose two previous Tour wins had come in play-offs, then fell out of it after hitting his drive into a bush on their third playing of the 18th and being unable to save par.
The extra significance of that was that it keeps Colin Montgomerie as Scotland's top player in the world rankings. It is a position he has held since 1991, but for how much longer remains to be seen.
Howell's 2006 Ryder Cup team-mates Paul McGinley and Darren Clarke, neither of whom have qualified for this coming week's Masters either, also look on the way back.
McGinley followed his third place finish in Korea by coming seventh on 13 under and Clarke's closing 68 lifted him to 24th.
Collated final-round scores (Gbr & Irl unless stated, par 71):
266 Gregory Bourdy (Fra) 63 65 68 70 (Gregory Bourdy won play-off at third extra hole), David Howell 67 68 67 64, Alastair Forsyth 65 69 66 66
267 Miles Tunnicliff 69 69 63 66
268 Gonzalo Fdez-Castano (Spa) 64 66 72 66
269 Damien McGrane 67 69 67 66
271 Charl Schwartzel (Rsa) 65 70 66 70, Paul McGinley 69 68 67 67
272 Steve Webster 67 66 70 69, Peter Baker 67 69 69 67, Jose Manuel Lara (Spa) 64 70 70 68, Simon Khan 65 67 72 68, Johan Edfors (Swe) 68 68 69 67, Andrew McLardy (Rsa) 66 68 72 66
273 Rory McIlroy 69 67 66 71, David Drysdale 71 67 66 69, Soren Kjeldsen (Den) 69 65 68 71, Pablo Martin (Spa) 63 71 69 70, Oliver Fisher 68 65 74 66
274 Felipe Aguilar (Chi) 68 68 71 67, Lee Slattery 66 68 68 72, Ulrich Van Den Berg (Rsa) 69 71 69 65, Mads Vibe-Hastrup (Den) 69 71 67 67
275 Gareth Paddison (Nzl) 68 68 68 71, Jan Are Larsen (Nor) 68 72 66 69, Martin Erlandsson (Swe) 69 66 71 69, David Dixon 68 68 70 69, Darren Clarke 68 70 69 68, Thomas Levet (Fra) 67 64 72 72
276 Brian Davis 71 68 69 68, Mikko Ilonen (Fin) 68 70 66 72, Stephen Gallacher 71 63 74 68, Jean-Francois Remesy (Fra) 70 63 74 69, Pelle Edberg (Swe) 69 68 72 67, Sam Little 69 68 68 71, James Kamte (Rsa) 65 72 69 70
277 Anthony Wall 69 70 67 71, Patrik Sjoland (Swe) 70 70 68 69, Zane Scotland (Gbr) 69 65 75 68, Marc Warren 71 69 69 68, Michael Jonzon (Swe) 64 70 71 72, Francois Delamontagne (Fra) 65 75 71 66, Fredrik Andersson Hed (Swe) 72 68 70 67
278 Robert Jan Derksen (Ned) 70 69 66 73, Ricardo Gonzalez (Arg) 69 70 68 71, David Park 72 67 68 71, Simon Dyson 67 66 70 75, Marius Thorp (Nor) 67 73 71 67
279 Jean-Baptiste Gonnet (Fra) 71 68 70 70, Ben Evans 67 71 72 69
280 Sam Walker 69 68 76 67, Robert Dinwiddie 70 70 71 69, Jarmo Sandelin (Swe) 70 68 74 68, Steven Jeppesen (Swe) 71 68 69 72, Fabrizio Zanotti (Par) 68 70 72 70, John Bickerton 71 68 70 71
281 Jamie Donaldson 70 67 73 71, Ross McGowan 70 70 68 73, Barry Lane 67 71 76 67
282 Nuno Campino (Por) 67 69 73 73, Matthew Millar (Aus) 68 69 74 71, Birgir Hafthorsson (Ice) 69 70 66 77, Matt Haines 72 68 73 69, Stuart Manley 67 68 76 71, Santiago Luna (Spa) 66 71 75 70, Simon Wakefield 68 71 71 72
283 Benoit Teilleria (Fra) 70 70 68 75
284 Sven Struver (Ger) 74 66 69 75, Marcel Siem (Ger) 71 66 74 73
286 Emanuele Canonica (Ita) 70 70 76 70
287 Paolo Terreni (Ita) 71 67 73 76, Peter Whiteford 74 64 75 74, Pedro Figueiredo (Por) 72 66 78 71, Steven O'Hara 70 70 77 70
288 Peter Gustafsson (Swe) 68 71 74 75, Ian Garbutt 71 69 75 73
290 Henrik Nystrom (Swe) 71 65 80 74