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'
|Mourinho has ´got to grips´ with United - Ferguson|
|Uganda v Mali: A lot at stake for Mali in shot-shy showdown|
|Napoli 1 Fiorentina 0: Callejon heads Partenopei into semi-finals|
|Bordeaux 1 Paris Saint-Germain 4: Cavani, Di Maria secure final berth|
|Watzke: Dortmund would consider €80m for Aubameyang|
|Togo 1 DR Congo 3: Kabananga´s goal streak continues as Ibenge´s men top group|
|Morocco 1 Ivory Coast 0: Alioui stunner sends holders crashing out|
|Romeu earns Southampton extension as Puel targets away goal|
|Sunderland striker Anichebe out for up to 10 weeks|
|Elneny wants to be an Arsenal legend ´like Thierry Henry´|
|Corini leaves Palermo as Ballardini is tipped for fourth return|
|Hernandez leaves Leicester for Malaga|
|Lukas PodGOALski...Gala forward nets five amid J-League links|
|CAS rejects Serbian appeal against Kosovo UEFA membership|
|Thiago back in Bayern training as Arsenal showdown looms|
|Thiago back in Bayern training as Arsenal showdown looms|
|Shearer´s Toon Army ´trump´ the POTUS|
|Rooney´s record may stand forever - Ferguson|
|Carrick expects full-strength United as Wembley return beckons|
|They insulted his mother and then there were monkey noises - Cyprien on Bastia Balotelli abuse|
|No Chelsea regrets for Sampaoli as Sevilla mount title challenge|
|Egypt v Ghana: Cuper backs Elneny to deliver in crucial Group D clash|
|James adds to Zidane´s injury woes at Madrid|
|Zidane wants fans behind Madrid after latest Ronaldo whistles|
|Mason ´continues to make excellent progress´|
|Allegri slams ´stupidity´ surrounding Buffon referee hug|
|Niang in talks over AC Milan exit, confirms Montella|
|Sunderland sign Lescott|
|China-bound Ramos completes loan switch to Granada|
|Rahman to miss ´several months´|
|Leekens quits after Algeria´s AFCON exit|
|Jese has firm Premier League offer, claims Las Palmas president|
|´I´m blessed with golden genes´ - Adebayor insists he is ready for new Premier League chance|
|Messi renewal progressing ´very, very well´ - Robert|
|Neuer expects Clement success at Swansea|
|Klopp calls for Liverpool enjoyment|
|Mustafi talks up Arsenal belief|
|Van Basten still against offside, slams ´nonsense in the media´|
|Rakitic dreaming of career-long Barcelona stay|
|Toure inspired by Ibrahimovic as he explains Chinese Super League snub|
|Kasperczak committed to attacking approach as Tunisia reach AFCON quarters|
|Slimani wants Algeria youngsters to learn from AFCON humiliation|
|Senegal 2 Algeria 2: Slimani at the double as Desert Warriors bow out|
|Zimbabwe 2 Tunisia 4: First-half glut seals progression|
|Adrian: I always wanted to return to Villarreal|
|Togo v DR Congo: Agassa could miss crucial game after vandals hit home|
|Extended Southampton stay on the cards for Sims|
|Bayern hoping for speedy Vidal return|
|Hull sign Markovic on loan from Liverpool|
|Wenger charged with misconduct by FA|
|Deulofeu joins AC Milan - and this time the deal is definitely done!|
|Henderson still playing through pain, reveals Klopp|
|Record-breaking Rooney reveals secret to longevity|
|No ulterior motive behind Van Dijk captaincy call - Puel|
|Carroll ignoring want-away Payet|
|Gerrard´s managerial ambitions ´wonderful news for Liverpool´ - Klopp|
|PSG interested in Guedes, confirms Emery|
|Barca lose Busquets to sprained ankle|
|Pulisic commits to Dortmund until 2020|
|Mason speaking after suffering fractured skull|
|Aubameyang blames poor preparation for Gabon AFCON exit|
|David Beckham returns to PSG|
|Morocco v Ivory Coast: Holders must beat old boss Renard as group reaches thrilling conclusion|
|Djilobodji charged over Fletcher incident|
|Cahill and Terry visit Mason in hospital|
|Allardyce onto second-choice transfer targets|
|Dortmund sign teenager Isak|
|Madrid confirm Modric and Marcelo injury blows|
|Vidal fears longer lay-off, targets return against Arsenal|
|Yaya Toure: Sterling should have dived!|
|Turan wants to see out Barcelona contract despite China talk|
|Impassioned Ibrahimovic attacks Rooney´s critics|
|´He has to lose weight´ – Mihajlovic angry after dropping Maxi Lopez|
|Lack of Liverpool signings frustrates Klopp|
|Suarez: Busquets difficult to replace for Barca|
|Depay impresses Lyon after debut|
|CSL? Rooney committed to United|
|Denis Suarez wants more goals after opening Barca account|
|Simeone bemoans inconsistency but says Atletico are improving|
|Mourinho won´t stand in the way of Rooney and CSL|
|Dzeko on target as Roma stay on Juve´s tail|
|Rakitic ready to cover for injured Busquets|
|Bale and Kane wish Mason well after serious injury|
|Busquets injury less severe than feared - Luis Enrique|