Azerbaijan secured their first win in FIFA World Cup qualifying, a hard-fought 2-0 triumph over Northern Ireland.
Michael O'Neill's charges, who had Jonny Evans sent off for the foul that led to Azerbaijan's injury-time second, were guilty of missing a host of chances at the Bakcell Arena in Baku as they slipped to a fifth defeat in Group F.
Rufat Dadashov had the Azerbaijan supporters on their feet in the 58th minute when he rounded off a neat move by side-footing beyond Roy Carroll.
And there was a late second goal when Mahir Shukurov capitalised on Evans' dismissal by curling home a free-kick from 20 yards.
Jamie Ward twice went close for Northern Ireland in the opening period, first forcing Kamran Agayev into a close-range save before scooping over the crossbar.
Martin Paterson was also guilty of wastefulness prior to Dadashov's strike when he dragged wide from eight yards and the Huddersfield Town striker also hit the bar with two minutes remaining.
O'Neill welcomed back Chris Brunt from suspension, meaning Niall McGinn dropped to the bench.
Azerbaijan included Vuqar Nadirov and Qara Qarayev in their starting XI, both having been named among the substitutes for the 1-1 draw with Israel in September.
Northern Ireland controlled possession in the early stages and Brunt nearly made a breakthrough in the ninth minute when he spun in the box and fired an effort at Agayev.
The West Brom winger was involved again soon after as his fierce 25-yard strike was beaten away by the goalkeeper.
Northern Ireland continued to press and Ward's 23rd-minute header from Paterson's centre forced a superb point-blank save from Agayev.
The visitors' profligacy was almost punished when Dadashov flashed an eight-yard strike wide of the post.
And Azerbaijan came even closer on 28 minutes as Rauf Aliyev hit a sweet back-post volley towards the near post, forcing Roy Carroll into a wonderful reflex save.
Northern Ireland finished the half the stronger and had two further chances to take the lead.
First Ward scooped a loose ball over the crossbar, before Paterson dragged wide after his strike partner's throughball put him one-on-one with Agayev.
Azerbaijan came out the stronger side after the break and Dadashov should have done better when he sidefooted Shukurov's cross wide.
Soon after, the forward did break the deadlock. Araz Abdullayev slid an intricate ball into Aliyev's path and his low cross was converted at Carroll's near post.
Northern Ireland looked for an immediate comeback and Gareth McAuley looped a header onto the roof of the net before Oliver Norwood curled a 30-yard free-kick just wide.
The away side became visibly frustrated in their efforts to break down an Azerbaijan side who were happy to defend their lead.
Paterson went closest in the 88th minute, receiving Steven Davis' pass before unleashing a vicious effort against the woodwork.
Evans duly saw red for an off-the-ball challenge on Aliyev and Shukurov's resulting free-kick put the result beyond doubt.
Azerbaijan finish their campaign with a home fixture against Fabio Capello's Russia on Tuesday, while Northern Ireland travel to Israel looking to avoid finishing bottom of the group.
|Coach: B. Vogts|
for V. Nadirov 46'
for A. Abdullayev 82'
for R. Dadaşov 90+3'
|Wanted man Sukur denounces coup|
|´Everyone knows my best position´ - Sturridge unhappy at wide role|
|Villa says Alcacer ´knows what to do´ amid Barcelona links|
|Solo ´saddened´ by United States axing|
|Drinkwater signs new Leicester deal|
|Spanish clubs dominate as history beckons for Ancelotti - the Champions League in numbers|
|Lopes sets sights on Lille silverware and Portugal breakthrough|
|´A scholar and a monster´ - Surgeon hails ´unique´ Ronaldo|
|MLS Review: Altidore scores as Toronto move top in east, Galaxy rally|
|CONCACAF Champions League Review: Tigres win, Dallas held|
|Victory lure Rojas back to Melbourne|
|Chaplow suspended two games for verbal abuse, denies homophobia|
|Eduardo farewells Dinamo Zagreb amid Chelsea speculation|
|Zidane shoud give James more respect - Asprilla|
|Solo suspended from USA women´s team for six months|
|Guardiola understands fans unhappiness over Hart situation|
|Burnley and Middlesbrough sent packing from League Cup|
|Coleman baffled by Ramsey´s treatment at Arsenal|
|Six of the best for Gladbach as Rostov rout Ajax|
|Leicester face Chelsea, Northampton host United in League Cup third round|
|Cillessen set to fly out to Barca to complete move|
|Guardiola hails ´legend´ Hart as Bravo wait in the wings|
|Emotional Hart edges towards City exit|
|Manchester City 1 Steaua Bucharest 0 (6-0 agg): City ease through amid Hart-felt goodbyes|
|Ronaldo working hard for Madrid return|
|Pique warns of European Super League dangers|
|AFC Champions League: Damjanovic inspires Seoul, Wanderley puts Al Nasr in charge|
|Rauball re-elected as German league president|
|Cillessen returns for Ajax despite Barcelona talk|
|Surgery for Pereira after De Rossi horror challenge|
|Hart set for City farewell against Steaua|
|CAF Champions League Review: Wydad draw at ZESCO to earn top spot|
|Retiring Keane in Republic of Ireland squad for final time|
|Sion in talks to sign Liverpool outcast Balotelli, claims club president|
|Athletic´s Laporte not distracted by Barcelona visit|
|Keane announces international retirement|
|Clarke named FA chairman|
|Neuer: Schweinsteiger remains one of world´s best|
|Bielsa would call me before coming to Marseille - Passi|
|Watford bring in Janmaat from Newcastle|
|FIFA opens adjudicatory proceedings against disgraced African football officials|
|European Super League could cause ´war´|
|Sampdoria pounce for Praet|
|Zaza agent confirms Napoli talks but rules out loan move|
|No Grigg in Northern Ireland´s World Cup qualifying squad|
|Cahill reflects on ´amazing´ Melbourne City debut|
|Europa League must take priority, Recoba tells Inter|
|Saint-Etienne swoop for Saivet and Veretout|
|Ronaldo: Pepe was the best player at the Euros, not Griezmann|
|Schweinsteiger: Manchester United my last club in Europe|
|Dante sees Nice as a positive move|
|Pique: Barcelona by far the best in Spain|
|Pique backs Stones for success under Pep|
|Coleman dismisses Premier League talk|
|Spurs want Calhanoglu, claims agent|
|Bony an ´option´ for Bilic|
|Leverkusen cannot challenge Bayern, says Ballack|
|Pallotta blasts ´disgusting´ referee after Roma defeat|
|Badstuber taking his time after injury nightmare|
|Conte: Terry return between him and Allardyce|
|We beat Bayern to Dembele - Watzke|
|Wanderers bring back Bulut|
|Moyes rules out Kone exit|
|CONCACAF Champions League Review: Whitecaps, Pachuca win big|
|Bale: I´ll never forget this year|
|Griezmann: I deserve Best Player in Europe Award|
|No surgery for Ayew as West Ham target December return|
|Villarreal did all they could to make it through - Escriba|
|Spalletti rues lack of Roma discipline|
|Conte: Chelsea must learn to kill matches|
|Watford and West Brom crash out of League Cup|
|My longest 90 minutes as a coach - Rodgers|
|AFC Champions League: Goalless draws leave quarter-finals on a knife edge|
|Klopp hopeful over Can injury|
|Champions League play-offs: Nine-man Roma crash out as Monaco edge Villarreal|
|Henderson hails ´outstanding´ Mane after Burton thrashing|
|Chelsea 3 Bristol Rovers 2: Conte´s side survive scare thanks to Batshuayi double|
|Hapoel Be´er Sheva 2 Celtic 0 (4-5 agg): Visitors survive Israeli scare|
|Burton Albion 0 Liverpool 5: Sturridge at the double in Reds rout|
|Leverkusen sign Austria star Dragovic|
|Sakho in the clear as WADA opt against appeal|
|Enyimba 3 Mamelodi Sundowns 1: Udoh brace secures CAF Champions League win|
|Pulisic and Ramos on target as Dortmund wrap up Bundesliga preparations|
|Calleri hoping for Tevez advice|
|Defour hoping for Belgium recall|
|Alaba warns against complacency as Bayern begin Bundesliga defence|
|Bravo arrives in Manchester ahead of City move|
|Dyche backs Gray after striker´s apology for homophobic tweets|
|Gray charged by FA over homophobic tweets|
|Pique: Olympic gold proves Neymar is one of world´s best|
|Marin makes Olympiacos move|
|Zidane arrival the catalyst for one of my best seasons - Ronaldo|
|Moyes ´worried´ about Mannone elbow injury|
|Sidibe rejected Arsenal over playing-time fears|
|Guardiola: Toure could feature against Steaua|
|Hernandez out for two weeks after falling down stairs|
|Bravo nearing City move, admits Guardiola|
|Ballack impressed by Dortmund signings but still backing Bayern|
|Lucescu questions De Boer tactics|
|Milan reject Chelsea bid for Romagnoli|
|Dortmund know how to treat Gotze - Ballack|
|Shevchenko: Bacca must improve consistency|
|´If you heed 100 idiots you will go crazy´ - Bauza on Messi return|
|Valdano relieved over Messi U-turn|
|Nordfeldt in line for loan move after signing fresh Swans deal|
|Dante joins Nice from Wolfsburg|
|De Boer expects fierce fight for Barca number-one spot|
|Newell´s confident over Messi return|
|Stoke confirm Jones interest|
|MLS ´attractive´ to Rooney - Timbers owner|
|Burke re-signs with West Ham|
|Sassuolo rejected Balotelli - CEO|
|Valencia coach Ayestaran rules out Mustafi sale|
|Allardyce plans Guardiola talks over Hart|
|Cahill warns rivals over City attack|
|Allardyce open to Terry England return|
|Drogba dismisses Villa rumours|
|Tuchel pleased despite Dortmund wastefulness|