Both teams are locked together on four points from five games so far, but a Scotland defeat would result in automatic relegation; Poland can afford to draw.
Match preview
After putting a first point on the board last month, by holding Group 1 leaders Portugal to a 0-0 draw, Scotland went one better on Friday night, when their long wait for a win finally ended at Hampden Park.
Steve Clarke's side lay bottom of the table and were in danger of heading straight back down to League B with one game remaining, but returning hero John McGinn stepped off the bench to score a late winner against 10-man Croatia.
Not only did his emphatic finish ensure that Scotland's survival fight would go on until the final matchday, but it also kept their slim hopes of qualifying for the Nations League's knockout phase alive.
Clarke later admitted that his side had not been at their best, with veteran goalkeeper Craig Gordon making several saves as Croatia defied their numerical disadvantage in Glasgow, but he was clearly relieved to end his nation's longest winless run on home turf.
Having also halted Scotland's longest streak without a competitive victory - a total of 10 games - Clarke and co can now approach Monday's finale with their demotion destiny in their own hands.
A draw in Poland will prevent them losing League A status and secure a relegation playoff in March; furthermore, a Croatia defeat to Portugal would mean that another Scottish success might even earn an unexpected top-two finish, depending on goal difference.
While Scotland's dreams of a quarter-final spot are still alive, Portugal are already through as group winners, and Croatia just need a point to guarantee progress, the only team totally out of contention is Poland.
The Poles were ultimately overpowered by their Portuguese counterparts on Friday, despite keeping the scoreline goalless at half time, as Rafael Leao made the breakthrough with a 59th-minute header and Cristiano Ronaldo scored twice in a 5-1 away defeat for the Bialo-Czerwoni.
Substitute Dominik Marczuk netted a consolation goal late on, but they have now sunk to the foot of the standings and a spectacular comeback win in Scotland remains their only Group 1 victory to date.
They also scrapped out a spirited 3-3 draw with Croatia, but Michal Probierz has not seen his side keep a single clean sheet in any of their last 10 matches, conceding at a rate nearing three goals per game in this season's Nations League.
Now, their task is quite clear: Poland will enter the playoffs if they win or draw their final fixture - the latter result would save them by virtue of a superior head-to-head record with Scotland - but another loss will see them relegated.
Poland Nations League form:
W
L
L
D
L
Poland form (all competitions):
D
W
L
L
D
L
Scotland Nations League form:
L
L
L
D
W
Scotland form (all competitions):
L
L
L
L
D
W
Team News
Despite the quick turnaround from Friday's game at Hampden, Steve Clarke is set to pick a similar Scotland XI to that which lined up against Croatia, given his team's Nations League fate is at stake.
Therefore, teenage winger Ben Doak - who played a large part in creating John McGinn's goal - should continue to feature in the final third, alongside Ryan Christie and Scott McTominay. Still short of full fitness, McGinn may again start on the bench.
The identity of who they will support remains in question, as the withdrawal of Torino striker Che Adams has left Tommy Conway, Lyndon Dykes and Lawrence Shankland vying to lead the line - Conway started last time out, but Dykes replaced him during the second half.
Meanwhile, Poland are missing captain and all-time top scorer Robert Lewandowski, who has been sidelined by a back injury; Inter Milan midfielder Piotr Zielinski will skipper the side in the Barcelona striker's absence.
Arkadiusz Milik is also out of action, so Karol Swiderski and Mateusz Bogusz are the main contenders to partner Krzysztof Piatek up front: Swiderski was prevented from appearing as a substitute in Portugal after an official spotted he had not been registered to play, but the Charlotte FC forward will be eligible for Monday's match.
With Hellas Verona defender Pawel Dawidowicz unavailable this month, either Kamil Piatkowski or Sebastian Walukiewicz should join Jan Bednarek and Jakub Kiwior in the hosts' back three.
Poland possible starting lineup:
Bulka; Piatkowski, Bednarek, Kiwior; Bereszynski, Urbanski, Zielinski, S. Szymanski, Zalewski; Swiderski, Piatek
Scotland possible starting lineup:
Gordon; Ralston, Souttar, Hanley, Robertson; McLean, Gilmour; Doak, McTominay, Christie; Dykes
We say: Poland 2-1 Scotland
These nations played out a five-goal thriller back in September, and more goals could flow in Warsaw, as the home side are particularly shaky at the back.