I have still a few more! 
Let’s start with Nanda, the Buddha’s maternal cousin and half-brother.
In SN21.8 we encounter him wearing fancy outfit and makeup, and the Buddha has to remind him of what is the proper conduct for a monastic. The reason behind this behavior is revealed in Ud3.2, where we learn that he is very much in love with his former wife, “the finest lady of the Sakyan land”. He even thinks about disrobing. The Buddha takes him for an outing to the gods of the 32, where he can compare his “finest lady” to the heavenly nymphs, and looses taste for her.
The Buddha’s, “Rejoice, Nanda, rejoice! I guarantee you five hundred dove-footed nymphs”, inspires him to stay in robes and practice for future heavenly pleasures—until he is fed up with his fellow monks teasing him because of that. So finally he “does what needs to be done”, and realizes awakening. He’s even praised as a model for monastic life in AN8.9.
Another one I’d like to mention is the Buddha’s former charioteer, Channa. He too receives a special treatment by the Buddha, which the latter orders on his deathbed, and Ananda applies it later.
The treatment is called “the divine punishment”, and it consists in a treatment that the Buddha earlier explained to the horse trainer Kesi to be equivalent to “killing” that person (AN4.111). “For it is killing in the training of the Noble One when the Realized One doesn’t think they’re worth advising or instructing, and neither do their sensible spiritual companions.”
So after the Buddha’s death Ananda travels to the place where Channa lives, and as that one is a bit temperamental, he goes together with 500 monks. He transmits the Buddha’s message: “Channa may say what he likes, but the mendicants should not correct, advise, or instruct him.”
And Channa drops … not dead, but unconscious, which is perhaps not that far away. The story is told in the 21st vinaya Khandhaka.
And the cure is quite effective. Channa changes his ways and finally in SN22.90 receives a teaching by Ananda. He then thanks him for his efforts:
“Reverend Ānanda, this is how it is when you have such venerables as spiritual companions to advise and instruct you out of kindness and sympathy. And now that I’ve heard this teaching from Venerable Ānanda, I’ve comprehended the teaching.”