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So, all Potterheads like me know that Slughorn worked during Harry’s sixth year, and some think he worked during James and Lily’s years, but is it possible that he worked with Dumbledore at other times?

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    There is no "some think he worked during James and Lily's years". The books (and the movies too, if memory serves) make it clear that he knew Harry's parents. – Jenayah Feb 11 at 21:46
  • youtu.be/fYzm3nIEOd0?t=54 – Valorum Feb 11 at 22:32
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Yes, they taught when Tom Riddle attended.

Dumbledore and Slughorn both were teachers at Hogwarts when Tom Riddle was a student there.

“People wouldn’t like to think we’ve been chatting about Horcruxes. It’s a banned subject at Hogwarts, you know … Dumbledore’s particularly fierce about it …”
- Harry Potter and the Half-Blood Prince, Chapter 23 (Horcruxes)

At that time, Dumbledore was the Transfiguration teacher, as the Tom Riddle in the diary mentioned.

“Only the Transfiguration teacher, Dumbledore, seemed to think Hagrid was innocent. He persuaded Dippet to keep Hagrid and train him as gamekeeper.”
- Harry Potter and the Chamber of Secrets, Chapter 17 (The Heir of Slytherin)

Slughorn taught potions, and doesn’t seem to have ever taught any other subject at Hogwarts.

“Professor Slughorn,’ Slughorn stood up, his bald head gleaming in the candlelight, his big waistcoated belly casting the table below into shadow, ‘is a former colleague of mine who has agreed to resume his old post of Potions master.”
- Harry Potter and the Half-Blood Prince, Chapter 8 (Snape Victorious)

Slughorn taught Potions while Dumbledore was headmaster.

Slughorn was still teaching when James Potter and Lily Evans attended Hogwarts.

“My mother’s eyes, yeah.’ Harry had heard it so often he found it a bit wearing.

‘Humph. Yes, well. You shouldn’t have favourites as a teacher, of course, but she was one of mine. Your mother,’ Slughorn added, in answer to Harry’s questioning look. ‘Lily Evans. One of the brightest I ever taught.”
- Harry Potter and the Half-Blood Prince, Chapter 4 (Horace Slughorn)

He was still teaching potions, as he mentioned Lily’s ability.

“Good Lord, it’s clear you’ve inherited your mother’s talent, she was a dab hand at Potions, Lily was!”
- Harry Potter and the Half-Blood Prince, Chapter 9 (The Half-Blood Prince)

By then Dumbledore was Headmaster, since he became Headmaster before Lupin was due to start Hogwarts, the same year as Snape, James, Lily, Sirius, and Pettigrew all started.

“But then Dumbledore became Headmaster, and he was sympathetic. He said that, as long as we took certain precautions, there was no reason I shouldn’t come to school …’ Lupin sighed, and looked directly at Harry. ‘I told you, months ago, that the Whomping Willow was planted the year I came to Hogwarts. The truth is that it was planted because I had come to Hogwarts.”
- Harry Potter and the Prisoner of Azkaban, Chapter 18 (Moony, Wormtail, Padfoot and Prongs)

Slughorn was never in the Order.

However, Dumbledore and Slughorn didn’t work together in the Order of the Phoenix because Slughorn never joined. He wasn’t in the photo of the original Order, and with his clear refusal to join the reformed Order, it’s highly unlikely he’d ever have joined either.

“Still … the prudent wizard keeps his head down in such times. All very well for Dumbledore to talk, but taking up a post at Hogwarts just now would be tantamount to declaring my public allegiance to the Order of the Phoenix! And while I’m sure they’re very admirable and brave and all the rest of it, I don’t personally fancy the mortality rate –”
- Harry Potter and the Half-Blood Prince, Chapter 4 (Horace Slughorn)

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    Is this what the OP meant though? Surely any "Potterhead" would know this too. I was thinking of "worked with" in the sense of something like the Order, outside of just being Hogwarts colleagues. – Rand al'Thor Feb 11 at 21:58
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    @Randal'Thor New users who call themselves a "Potterhead", include some name from the books in their username, etc. are generally younger and don't actually know as much as they like to think about the works, so I suspect this is exactly what they meant. – Anthony Grist Feb 11 at 22:28

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