Gareth Southgate's side fell to a very rare qualifying defeat at the hands of Czech Republic to leave them level with their conquerors at the top of Group A, although victory in Sofia could see them clinch a place at Euro 2020, the final of which they host at Wembley.
Southgate was just over a week away from being sacked as manager of Championship side Middlesbrough the last time England lost a qualifying match prior to Friday night.
Whereas disappointing results at major tournament have been a common theme of the past decade, the defeat in Prague - which England could have no complaints about following a drab and uninspiring performance - was their first during a European Championship or World Cup qualifying campaign for 10 years.
Czech Republic's triumph ended a 43-match unbeaten streak, not to mention England's perfect start to the campaign which had see them win four from four while scoring 19 goals in the process.
While the result was undoubtedly a shock considering England won the reverse fixture 5-0 in March, there had also been signs of Southgate's side not being quite as dominant as their record suggested - most notably in an unnecessarily topsy-turvy 5-3 win over Kosovo last month.
England's previously prolific attack failed to click in Prague which, coupled with increasingly obvious defensive deficiencies, allowed a Czech side placed 40 spots below them in the rankings to pull off a famous victory.
Defeat in Sofia would represent an even bigger shock considering Bulgaria sit rock bottom of Group A, nine points behind England and having failed to win any of their six outings so far.
Bulgaria are another 18 places below the Czechs in the FIFA rankings and have failed to win any of their last 10 games across all competitions - a run which will have stretched back more than a year by the time this match gets underway.
That run includes a 4-0 defeat at Wembley last month too, although they may take a sliver of confidence from the fact that they were able to register four shots on target in that match - better finishing this time around could help them get something from this meeting.
A goalless draw with Group A's other winless side Montenegro ended a four-match losing streak for Monday's hosts, but their last home outing saw them beaten by Kosovo and they are now looking to avoid successive defeats on home soil for the first time since 2012 - a three-match run incidentally started by England.
Bulgaria's own hopes of qualifying for Euro 2020 via this competition are now over, but if England do return to winning ways as expected in this match then they would seal their place at the tournament, so long as Kosovo also fail to beat Montenegro.
It is also 10 years since England last lost back-to-back away games in any competition and Southgate will have no doubt demanded a response from his side following such a lacklustre display last time out.
One issue which could overshadow all of that is the threat of racist chanting from those inside the stadium, though, with some England players hinting that they could walk off the field should such problems rear their ugly heads again.
It is a pre-match talking point which will hopefully be forgotten and made redundant by the time of the final whistle, but there has been precedent and plenty of eyes will be trained on how England players react if the situation arises.
Bulgaria form: DLLLLD
England form: WLWWWL
Southgate is likely to consider changes following the defeat in Prague, but captain and striker Harry Kane will retain his place having scored seven goals in five qualifiers so far - including a hat-trick in the reverse fixture.
The similarly in-form Raheem Sterling, who won the penalty Kane converted against the Czechs, is also expected to start again, leaving Marcus Rashford to battle it out with Jadon Sancho for the other spot in that front three.
Mason Mount impressed as much as could be expected considering how poor England were on Friday night and could be given the opportunity to earn his second England start, with the bulk of the changes likely to come in defence.
As for Bulgaria, captain Ivelin Popov should return to the side after missing out against Montenegro, with the 31-year-old by far the most experienced and highest-scoring player in the squad.
Indeed, only three other players have made 20 or more appearances for their country, while the next leading scorer from the current crop of players is Georgi Kostadinov on three.
Bulgaria possible starting lineup:
Iliev; Pashov, Dimitrov, Zanev, Nedyalkov; Kostadinov; Ivanov, Marcelinho, Malinov, Wanderson; Kraev
England possible starting lineup:
Pickford; Alexander-Arnold, Gomez, Maguire, Chilwell; J Henderson, Winks; Sancho, Mount, Sterling; Kane
We say: Bulgaria 1-4 England
Southgate will be expecting a response from his England side and the players have the quality to prove that the Czech Republic result was merely a blip. Things should be slightly tougher than they were at Wembley in the reverse fixture, but you would still expect England to win this match comfortably.