Imagine if there was a certain type of of Ki in Dragon Ball... let's call it Type-G for now... imagine if this Type-G Ki wasn't sensible in the usual way... that characters who possessed this Type-G Ki were unable to have their strength measured.
Now imagine if you had a character... let's call him Salagadoola... who absorbed a Type-G Ki user... character's might have difficulty accurately measuring the strength of Salagadoola. His measurable Ki may seem lower than his actual total... it would almost seem deceptive.
...if only things worked out that cleanly...
When Goku says the "like a lie" "...I think I probably..." line, he is unable to fully gauge Majin Buu's strength... but was also not exactly trying to win in the first place. When he says the "Now I can say" line, he has a grasp on that strength.
For the "Now I can say" to be a big reveal that he knew he could beat him all along would require his motive behind that to also be revealed... but that motive was already long-revealed after the first encounter: He wanted to leave things to the next generation. If he knew he could beat Buu earlier, it would've changed nothing... there's literally no reason for him to lie about that.