Both sides lost twice last month to sink to the foot of League C Group 1, leaving them six points adrift ahead of this week's meeting in Tallinn.
Match preview
Following their success in the 2022-23 Nations League, when they topped a League D group also containing Malta and San Marino without dropping points, Estonia were pitched into a tough four-team section for this season's campaign.
Having suffered an opening-day defeat to Slovakia on home turf, three days later they trailed by three goals before half time against Sweden - relative powerhouses at Europe's third level.
Despite having Kevor Palumets sent off later on, the Blueshirts limited their losses in Solna, but after a 3-0 defeat they have no points and no goals on the board in Group 1.
Estonia's feats in the last Nations League not only earned them promotion but also a place in the Euro 2024 playoffs; however, a 5-1 semi-final defeat by Poland swiftly curtailed dreams of a first major finals appearance.
While missing out on the Euros, they claimed the Baltic Cup by beating the Faroe Islands and Lithuania, but in major international competition they have gone 16 games without victory.
New national team boss Jurgen Henn is now concerned with getting the better of Azerbaijan in the teams' upcoming contests; otherwise, a fourth-placed finish would mean automatic demotion from League C.
On their most recent trip to Tallinn, Azerbaijan left with maximum points, winning 2-0 on Estonian soil after drawing 1-1 in Baku during Euro 2024 qualifying.
After failing to reach this year's finals in Germany, the Azeri FA turned to veteran coach Fernando Santos, who won both the Euros and the inaugural Nations League with Portugal but has since had less success in charge of Poland and Besiktas.
Azerbaijan finished second in their group in the last edition of the Nations League, and replicating that result this time would bring a chance of achieving promotion to League B through the playoffs.
However, Santos oversaw successive defeats against Sweden and Slovakia last month, with his team losing 3-1 to the Swedes on home turf before going down 2-0 in Kosice three days later.
Therefore, picking up points against either Estonia or Slovakia before next month's Group 1 finale is essential - if not, Azerbaijan face slipping down to Europe's fourth tier.
Estonia Nations League form:
L
L
Estonia form (all competitions):
L
L
W
W
L
L
Azerbaijan Nations League form:
L
L
Azerbaijan form (all competitions):
W
D
L
W
L
L
Team News
Estonia coach Jurgen Henn has some selection headaches to resolve on Friday, as first-choice striker Rauno Sappinen has withdrawn due to illness, while the latter's Flora Tallinn teammate Mark Anders Lepik is injured.
Furthermore, key midfielder Kevor Palumets must serve a suspension for his dismissal against Sweden, possibly opening the door to Markus Poom of Shamrock Rovers.
Azerbaijan will seek inspiration from Turkey-based striker Renat Dadashov and Qarabag winger Toral Bayramov, the latter of whom spectacularly missed a penalty against Tottenham Hotspur in the Europa League last week.
Meanwhile, Mahir Emreli has been brought back into the squad, despite failing to get off the mark for Nurnberg in the 2. Bundesliga this season.
Captain Emin Mahmudov is the Azeris' leading active scorer with 10 international goals to date, and the Neftci Baku playmaker should start in midfield.
Estonia possible starting lineup:
Hein; Paskotsi, Tamm, Mets, Schjonning-Larsen; Miller, Poom, Shein, Sinyavskiy; Tamm, Anier
Azerbaijan possible starting lineup:
Jafarov; A. Huseynov, Mammadov, B. Huseynov, Jafarquilyev; Isayev, Jamalov; Kokcu, Mahmudov, Bayramov; Dadashov
We say: Estonia 0-1 Azerbaijan
Even though Azerbaijan do not pick up many points on the road, they should have the firepower to outgun an ailing Estonia side that lacks depth in the final third.