With eight races remaining, the Spaniard is 46 points behind Red Bull's triple world champion and overall leader Sebastian Vettel with some of the German's most dominant tracks coming up in Asia and the Middle East.
Monza is a special place for Vettel, having taking his first Formula One win there with tiny Toro Rosso in 2008, but Red Bull have triumphed there only once - in 2011 - and team principal Christian Horner spoke in Belgium of it as a potential 'Achilles Heel' for his car.
"We don't expect, maybe, to be that strong (at Monza) but let's see," Vettel said after winning at Spa last month for his fifth victory of the year.
There is more optimism - and burden of expectation - at Ferrari, the most successful constructor by far at their home circuit with 18 wins over the years compared to McLaren's 10.
Alonso won in 2010, and was third in 2011 and 2012. He also won with McLaren in 2007 and was second in 2005 with Renault.
Sunday's race, at a circuit haunted by the ghosts of history with the decaying 1950s banking quietly crumbling beyond the modern track, will sound a last post for Formula One's V8 engine in Europe and locals would argue that a win for the sport's oldest and most successful team would be a fitting farewell.
"It's an important weekend for us, for the team," agreed Alonso, who will have to be at his very best to line up on the front row for the first time in 22 races and more than a year of trying.
"Last year we were very close to repeat the victory that we got also in 2010, so we arrive fully motivated again and in Monza we would like to give some smiles and some satisfaction to the tifosi and we will try our best," said the double champion.
MASSA MOTIVATION
Massa, whose future is under more scrutiny now that Red Bull have decided their 2014 line-up, has made only one appearance on the podium this season - a third in Spain - and has not won a race since 2008.
There will be no shortage of motivation for Massa, even without the pressure of fighting to keep his job, in a race without Italian drivers.
"I am Brazilian but my family came from Italy so this is something of a home race as I have an Italian passport and our family has something of an Italian lifestyle," he told the Ferrari website (www.ferrari.com) this week.
"This all adds up to a very special race for me."
Toro Rosso's Australian Daniel Ricciardo, who will be Vettel's team mate at Red Bull next season as replacement for departing compatriot Mark Webber, also has an Italian passport but cannot count on too much support even if he currently races for an Italian-based team.
The Monza fans are famed for their passion as well as their complete devotion to all-things Ferrari, their enthusiasm more like a football crowd venting its ire at anyone on the podium not dressed in red.
Lewis Hamilton was booed by them last year when he won for McLaren, with Ferrari-powered cars second, third and fourth, and cannot expect much to have changed should he return triumphant with Mercedes.
The 2008 world champion is chasing his fifth pole in succession to give himself the best shot of a repeat win to close the gap on Vettel and Alonso after being left trailing by both rivals at Spa and finishing third.
The driver starting on pole has won eight of the last 10 races at Monza and only three current drivers - by coincidence the top three in the championship - have won there before. None of them has so far won twice in Italy for the same team.
"We will use a refined version of the low-drag package introduced at Spa. We hope to see an improvement in race pace after the lessons we learned over the race weekend in Belgium," said Mercedes motorsport head Toto Wolff.
(Reporting by Alan Baldwin in London, editing by Pritha Sarkar)
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