The added pressure of knowing Porto won their match on Saturday will be nothing new for Benfica, but knowing that this could be the match of the season for the hosts will help to make things slightly more difficult.
For a Benfica fan, it almost seems as if every opponent's match of the season comes against them, but regardless of all of that, the Aguias need to focus on their objectives and not worry about everything else.
Monday's three points could really help both sides, but for two very different reasons.
Maritimo is looking to make their way up the league table, and a victory at home over Benfica would put them even on 37 points in sixth place with V. Guimaraes. One point out of a European spot would be ideal for Pedro Martins' squad, with three matches remaining.
Benfica's need for the three points comes down to reclaiming their four point lead over their fiercest rivals in all of Portugal. A slip up for Jorge Jesus' side would really send this league into a very heated battle, knowing that the Lisbon side will travel to Porto in two weeks time. A victory against the Madeirenses could give Benfica the opportunity to potentially celebrate the league title against Porto in May.
One important stat for Benfica heading into this match will be the fact that they have not lost to Maritimo away for the league in 11 years.
We need to go all the way back to the 2001/02 campaign when the hosts, who were managed by Nelo Vingada, defeated Jesualdo Ferreira's side 3-2. Goals from Gaucho and former Benfica player Daniel Kennedy were enough to see off Pedro Mantorras' two goals.
Since that defeat, Maritimo has drawn three and lost seven. The last four have gone in Benfica's favor, with a score line of 0-13 for the Aguias.
With fans looking at this match as the potential title match, Jorge Jesus has made it clear that their are still three matches remaining after Monday night.
"It is an important match," said the Benfica manager. "All the matches are more important at this point in the campaign. We do not feel like this is the title match, but it is very important as was our last match against Sporting."
Traveling without Argentine international Nico Gaitan, Jesus confirms that he may make some changes in the squad given his players fitness levels.
"The players give us an idea of their conditioning levels, and it is at that point that we need to make decisions. It is due to this that we may make some changes tomorrow that some people may not be expecting."
The Benfica manager's approach to take some pressure off of his players when stating that it is not the title match, is the opposite approach of which Maritimo's Rafael Miranda took.
"It is the match of the season for Maritimo," Miranda told reporters in a press conference. "It is an important match and we want to at least grab a point."
"This match is clearly important for our opponent, but for us, this is the most important match as it is the first of our last four matches in the league."
Failure to grab points for Maritimo would not put them completely out of the race for a Europa League spot, but it would make things extremely difficult heading into the final three matches.
As for Benfica, anything less than a victory would not knock them out of first place, but it would certainly inject some unneeded nerves into the squad, with three matches remaining. With two of their last three coming at home against Estoril and Moreirense in that order, the Lisbon side should feel confident about reclaiming the Portuguese title after a two year drought. Grabbing their fifth consecutive victory in league play at the Estadio Dos Barreiros on Monday would be a massive step for the Aguias.
12-15-12 Benfica 4-1 Maritimo
04-21-12 Benfica 4-1 Maritimo
02-05-12 Benfica 3-0 Maritimo (League Cup)
12-11-11 Maritimo 0-1 Benfica
12-02-11 Maritimo 2-1 Benfica (Portuguese Cup)
02-27-11 Benfica 2-1 Maritimo
Maritimo 1-2 Benfica