The Blues have benefited from some shocking officiating to seal last-gasp 2-1 wins in their last two matches, with poor decisions handing them victory in Wednesday night's Champions League clash with Benfica and Saturday's Premier League game with Wigan.
There have been other lucky escapes since Di Matteo was appointed caretaker manager, something the Italian admitted the sacked Andre Villas-Boas did not enjoy.
"If you look at this team this season, we haven't had exactly a lot of luck," he said. "Sometimes, you need a little break, but I don't think we had actually many this season, to be honest."
That begged the question why Di Matteo was blessed in a way Villas-Boas had not been.
He added: "Well, you need to deserve it. I think you need to deserve your luck.
"It doesn't just come if you sit at home."
Di Matteo said on Friday Chelsea could not afford to drop points against Wigan but he claimed yesterday a draw would not have spelt the end of their top-four ambitions.
"No, I don't think it would've been finished," said Di Matteo, whose side took advantage of Tottenham's failure to win at Sunderland.
"Until theoretically it's impossible, I think we're going to try.
"Spurs drew, so you're going to get a result that you maybe don't expect from teams."
Reiterating he felt the race for a Champions League spot would go to the wire, he added: "We are very, very delighted that we are a little bit closer, because obviously there are always less games now to play.
"But it's still going to be a difficult task."
Chelsea may have ticked off one more Premier League game but their punishing schedule continues with Monday's west London derby at Fulham.
Di Matteo made seven changes yesterday but pointedly did not rest matchwinner Juan Mata, who has started all but one of the Italian's 10 games in charge.
Summer signing Mata is beginning to look tired, but Di Matteo said: "He's a very important player for us. He unlocks situations for us and he's enjoying himself.
"He's a young man, he's got plenty of energy and I've given him a rest here or there. I've taken him off a few times."
Di Matteo would possibly be more inclined to give Mata a breather were Chelsea's other trickster, Daniel Sturridge, not proving more of a liability than an asset at present.
The 22-year-old was at his most frustrating on Saturday and the Stamford Bridge crowd were noticeably on his back before he was substituted.
But Di Matteo said: "I didn't hear that from the fans.
"I was planning to do the change a couple of minutes before that already, so it wasn't because of anything like that."
Admitting Sturridge too often picked the wrong option, he added: "It's about decision-making maybe. But I said before in the past we tend to forget that it's his first full season with us.
"He's still a young man and we still all have to learn and develop."
Di Matteo is expected to make more wholesale changes on Monday, after which Chelsea have what could end up being their only six-day break before the end of the Premier League season.
Asked if that was a relief, Di Matteo scoffed: "Relief? No, I wouldn't describe it as a relief.
"I'm already thinking about Fulham and I haven't thought actually about what's going to happen a couple of days after that."
