But Ferrari chose to sign the returning 2007 title winner Raikkonen for this year, with Massa now insisting he is not surprised the Finn is struggling alongside Spaniard Alonso.
Massa told Germany's Auto Bild he thinks Raikkonen is "maybe not quite as good" as Alonso.
In fact, the 33-year-old said he had the measure of the 'iceman'.
"In 2007 he was champion, but until Monza I was ahead of him," said Massa, recalling his battle with Raikkonen some seven years ago.
"Unfortunately, in our team we had an agreement that Monza would decide who is the number 1, and I was ahead of Kimi when I had a problem with my car.
"In 2008 I was in front of him," Massa added, "and also up until my accident in Hungary in 2009. Nevertheless, Kimi is world champion, and I'm not."
However, Massa insists he has no regrets about losing his Ferrari seat for 2014 and moving to Williams.
"It was absolutely the right move," he told Germany's Sport Bild.
"Looking back now, I am even glad that Ferrari did not want me because it opened the way for coming to Williams.
"I'm pretty relaxed, motivated, the team respects me," Massa explained. "You know, sometimes a change is good.
"I'm older but I feel young again. I'm ready to fight and work hard. I regret nothing," he added.
Massa also admitted that he doesn't miss the ultra high-pressure of wearing a red suit.
"Absolutely not!" he exclaimed. "At Ferrari it was huge -- if you don't win, you have a big load on your shoulders.
"You try to use it as positive energy, but you are constantly tense.
"Here at Williams I think only about the racing, which is better," said Massa.