Azerbaijan secured the first win of their World Cup qualification campaign with a hard-fought 2-0 triumph over Northern Ireland on Friday.
Michael O'Neill's charges, who had Jonny Evans sent off for the foul that led to the hosts' injury-time second, were guilty of missing a host of chances at the Bakcell Arena in Baku as they slipped to their fifth defeat in Group F.
Rufat Dadasov 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 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 Dadasov's strike when he dragged wide from eight yards and the Huddersfield striker also hit the bar with two minutes remaining.
O'Neill welcomed Chris Brunt back from suspension, meaning Niall McGinn dropped to the bench.
Azerbaijan boss Berti Vogts, meanwhile, 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.
The visitors controlled possession in the early stages and Brunt nearly forced 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 Dadasov 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.
But 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 through ball put him one-on-one with Agayev.
Azerbaijan came out the stronger side after the break, though, and Dadasov should have done better when he sidefooted Shukurov's cross wide.
Soon after, however, 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.
Paterson went closest in the 88th minute, receiving Steven Davis' pass before unleashing a vicious effort against the woodwork.
But Evans then 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'
|Undermanned Lazio recall Perea|
|Ki wants South Korea to prove their superiority|
|Ghana´s Gyan wary of South Africa|
|Mashaba urges South Africa to attack|
|Benitez: Napoli deserved to win|
|Pacos de Ferreira 1 Benfica 0: Leaders fail from the spot|
|Serie A Review: Higuain at the double in controversial Napoli win, Udinese see off Empoli|
|I´m glad Rochdale haven´t made the news - Hughes|
|Getafe 2 Celta Vigo 1: Hosts come from behind for first win in 10|
|Real hit back at media reports over transfer dealings|
|Rochdale 1 Stoke City 4: Joy and angst for Bojan as Premier League side progress|
|Turkish Super Lig Review: Kuyt at the double in Fenerbahce win, Besiktas back on track|
|Senegal v Algeria: Morale is high, insists Gourcuff|
|Cassano leaves beleaguered Parma|
|Copa del Rey Preview: Atleti look to overturn Barca advantage, Espanyol wary|
|Atletico Madrid v Barcelona: Griezmann targets second-leg fightback|
|Sheffield United v Tottenham: Clough expects fired-up Spurs for second leg|
|Cape Verde 0 Zambia 0: Stalemate sends both sides out|
|Democratic Republic of Congo 1 Tunisia 1: Both teams qualify for quarter-finals|
|FA Cup fifth round: Middlesbrough handed Arsenal test|
|South Africa v Ghana: Must-win game for Mashaba´s men|
|Parma v Juventus: Serie A leaders strong favourites to reach semi-finals|
|Van Praag planning to stand for FIFA presidency|
|Inter snap up Brozovic|
|Van Persie unsure of long-term United future|
|Broken metatarsal rules El Shaarawy out for at least six weeks|
|FIFA: No disciplinary proceedings against Real|
|No Plan B if Guardiola goes - Rummenigge|
|Millwall take Hooiveld on loan|
|Chile v United States: Klinsmann has high hopes for young stars|
|Carver to lead Newcastle until end of season|
|Shenaishil taking positives from last-four exit|
|Neymar happy with life at Barca and Messi relationship|
|Lucas Silva ready for life at Real|
|Milan ´always with Inzaghi´ - Menez|
|Rodriguez living the dream at Real|
|Stielike expecting Australia in final|
|Mourinho not dwelling on Bradford defeat|
|Schweinsteiger under no pressure to extend Bayern contract|
|Herd heads to Wigan on loan|
|Inter defensive duo suffer hamstring tears|
|UAE coach Ali eyes Asian Cup final|
|Gattuso dreaming of managing Rangers|
|Fiorentina agree return of Gilardino on loan|
|Sakho hits back at critics|
|South Korea 2 Iraq 0: Kim books sixth Asian Cup final place|
|Sturridge could return against Chelsea|
|Zinnbauer backs Drobny as Hamburg first choice|
|Drogba targeting Chelsea stay|
|Postecoglou confident Australia squad can progress|
|UEFA does not have the courage to run against me - Blatter|
|Foster: Anichebe unplayable|
|Australia v UAE: Japan´s absence a boon for Asian Cup hosts|
|Milan v Lazio: Injury-hit visitors aiming for back-to-back wins|
|Trezeguet confirms retirement|
|No ´major problems´ with Nicolas Frey´s head wound|
|Strootman injury not "serious" - Garcia|
|No Paraguay, USA for retiring Riquelme|
|Saint-Etienne did not try to play football - Blanc|
|Primeira Liga Review: Sporting move within one point of Porto|
|La Liga Review: Parejo downs Sevilla, Resino starts with a point|
|Serie A Review: Juve go seven points clear as Roma draw again|
|Ligue 1 Review: Paris Saint-Germain and Lyon make Marseille pay for slip-up|
|Burkina Faso coach puts AFCON exit down to bad luck|
|Saint-Etienne 0 Paris Saint-Germain 1: Ibrahimovic scores in repeat performance|
|Shenaishil optimistic despite Kasim absence|
|Walcott: Goal has been a long time coming|
|DR Congo v Tunisia: Leekens warns against complacency|
|Congo 2 Burkina Faso 1: Thievy helps send 2013 runners-up crashing out|
|Gabon 0 Equatorial Guinea 2: Balboa and Iban put hosts through|
|McCarthy and Distin on road to recovery|
|Gil has hit the ground running - Lambert|
|Eredivisie Review: Ajax and Feyenoord lose ground after dour draw, Eagles secure big win|
|Wenger confirms Gabriel move is imminent|
|Eto´o presented to Sampdoria fans|
|Cape Verde v Zambia: Victory a must for 2012 winners to avoid elimination|
|Brighton and Hove Albion 2 Arsenal 3: Walcott and Ozil among the goals for holders|
|Mancini upbeat despite ´cruel´ late defeat|
|Pogba revelling in rich vein of form|
|Aston Villa 2 Bournemouth 1: Gil helps under-fire Lambert breathe easy|
|Defour dismissed after Standard Liege banner taunt|
|Allardyce relieved with scrappy West Ham win|
|Sturridge ´happy man´ after return to Liverpool training|
|Inter 0 Torino 1: Moretti ends unbeaten run for top-four hopefuls|
|Juventus 2 Chievo 0: Pogba inspires victory as leaders march on|
|Bristol City 0 West Ham 1: Super sub Sakho sinks City|
|Hughes in talks over new Stoke deal|
|Delph signs new contract|
|Chelsea v Liverpool: Mourinho demands League Cup response|
|Football League Preview: Derby eye top two, Cambridge back to reality|
|Nani not giving up on Old Trafford career|
|Perth Glory 3 Melbourne Victory 3: Leaders stage two-goal late comeback|
|Neymar: Barca have no interest in Real results|
|Milan defender Mexes apologises for red card|
|South Korea v Iraq: Strange lead-up for Shenaishil´s men|
|Lazio´s Djordjevic thanks well-wishers ahead of ankle surgery|
|Iran´s Asian Cup appeal dismissed by AFC|
|Cech urges Chelsea to clean up FA Cup exit ´mess´|
|Henderson: Liverpool are up for the cup|
|Edimar wants ´normal´ ban for Real star Ronaldo|
|Pellegrini defends misfiring City strikers|
|Australia ready for UAE - Sainsbury|
|Blanc takes positives from past|
|Inzaghi promises ´something different´ at Milan|
|Mexes sorry for seeing red|
|La Liga Review: Wins for top three|
|Vitoria Guimaraes 2 Gil Vicente 2: Last-gasp penalty salvages point for hosts|