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(some mild spoilers ahead)

In the books the Order of the Phoenix seems to be always on the losing side when fighting Death Eaters.

Some battles that are more or less lost:

  1. The battle in the Ministry at the end of book 5. The Order of the Phoenix was practically losing with most of them either incapacitated or dead. It was Dumbledore who came and saved the day.

  2. The battle in Hogwarts at the end of book 6. They could not stop the Death Eaters from reaching the tower and doing what they came for and they could not stop them from fleeing afterwards.

The only case where they 'win' is the Battle of the Seven Potters. At least it could count as a 'strategic victory' since their objective was to safely transport Harry. During the battle they are on the run the whole time.

Any canon evidence about battles/skirmishes won by the Order?

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    Keep in mind, of course, that we really don’t know that those were the only violent encounters between the two groups (and indeed, they almost certainly were not, particularly considering the first war). – Adamant Mar 17 '17 at 6:40
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    @Adamant Yeah but at the same time it was more like guerrilla warfare. Most of the time one group or the other was in hiding or refusing to fight out in the open. It was very cloak and dagger. I think there probably were other fights but there were hardly regular large-scale battles. Many of the Order members who died were killed in hit jobs rather than general duelling. – The Dark Lord Mar 17 '17 at 11:22
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    The battle of hogwarts at the end of Book 7? Pretty sure Dumbledore didn't come and save the day on that particular occasion. – DisturbedNeo Mar 17 '17 at 11:26
  • They tried to take Gran (Augusta Longbottom) away with just two Death Eaters, but Gran got the better fo them. This doesn't count because I don't think Gran was a member of the Order. – b_jonas May 12 '17 at 7:34
  • I mean, I guess you could count the battle of Hogwarts, since Dumbledore technically didn't intervene – albusseverus potter May 17 '17 at 20:37
19
+50

Some of these examples may be somewhat stretched or technically correct ones, but I'll definitely point out my assumptions in each case. I will also exclude the "Advance Guard" or Battle of the Seven Potters since the OP has already mentioned this.


Trio vs. Cafe Thugs

In Harry Potter and the Deathly Hallows, after escaping the attack on Bill and Fleur's wedding, the Trio - Hermione Granger, Ron Weasley and Harry Potter - arrive at Tottenham Court Road:

“Where are we?” said Ron’s voice.
Harry opened his eyes. For a moment he thought they had not left the wedding after all: They still seemed to be surrounded by people.
“Tottenham Court Road,” panted Hermione. “Walk, just walk, we need to find somewhere for you to change.”
-Harry Potter and hte Deathly Hallows, Chapter Nine (A Place to Hide).

After settling in a cafe (now known as the Luchino Café), the trio are confronted by a couple of Death Eaters - Anton Dolohov and Thorfinn Rowle. After a quick duel, the trio defeat the Death Eaters:

“I should’ve recognized him, he was there the night Dumbledore died,” he said. He turned over the darker Death Eater with his foot; the man’s eyes moved rapidly between Harry, Ron, and Hermione.
“That’s Dolohov,” said Ron. “I recognize him from the old wanted posters. I think the big one’s Thorfinn Rowle.”
-Ibid.

Details

  • Combatants - Order of the Phoenix:
    • Hermione Granger
    • Harry Potter
    • Ron Weasley
  • Combatants - Death Eaters:
    • Anton Dolohov, def
    • Thorfinn Rowle, def
  • Outcome:
    • Decisive Order of the Phoenix Victory

Wedding Party vs. Wedding Crashers

During the event of the attack on Bill and Fleur's wedding, there are many members of the Order of the Phoenix present. Given that most of them seem to make it out alive, I'd say that's a victory for them.

... the Patronus’s mouth opened wide and it spoke in the loud, deep, slow voice of Kingsley Shacklebolt.
“The Ministry has fallen. Scrimgeour is dead. They are coming.”
-Harry Potter and the Order of the Phoenix, Chapter Eight (The Wedding).

...

As they pushed their way across the dance floor, Harry saw cloaked and masked figures appearing in the crowd; then he saw Lupin and Tonks, their wands raised, and heard both of them shout, “Protego!”, a cry that was echoed on all sides —
-Harry Potter and the Deathly Hallows, Chapter Nine (A Place to Hide). [emphasis mine]

Details

  • Combatants - Order of the Phoenix:
    • Bill Weasley
    • Fleur Delacour
    • Charlie Weasley
    • Fred Weasley
    • George Weasley
    • Luna Lovegood
    • Harry Potter
    • Hermione Granger
    • Ron Weasley
    • Ginny Weasley
    • Elphias Doge
    • Arthur Weasley
    • Molly Weasley
    • Kingsley Shacklebolt
    • Remus Lupin
    • Nymphadora Tonks
    • Others
  • Combatants - Death Eaters:
    • Unknown, numerous
  • Outcome
    • Decisive Order of the Phoenix Victory

Showdown at the Wayne Malfoy Manor

Whilst on the run during the events of Harry Potter and the Deathly Hallows, the Trio are assailed, captured and finally brought to the Malfoy Manor. At which point they are questioned, tortured and attacked by many Death Eaters. They manage to escape with the help of the other Dumbledore - Aberforth.

This one's a little bit iffy, given that Dobby (who helped them escape) had been given to Aberforth by Albus and the two-way mirror had been purchased by Aberforth after Albus had told him what it was.

  • Combatants - Order of the Phoenix:
    • Dobby, killed
    • Aberforth Dumbledore
    • Luna Lovegood
    • Harry Potter
    • Hermione Granger
    • Ron Weasley
  • Combatants - Death Eaters:
    • Narcissa Malfoy, def
    • Draco Malfoy, def
    • Lucius Malfoy, def
    • Bellatrix Lestrange, def
    • Werewolf McWerewolfson (Fenrir Greyback), def
    • Scabior
  • Outcome
    • Minor Order of the Phoenix Victory

Trio vs. Gringott's

Well, more like Gringott's employees who are loyal to the regime and also "Travers" the Death Eater. The Trio (and Griphook) didn't so much defeat them in the traditional sense of the word, but they definitely got past them and thir protections on Gringott's. Even escaping the facility safely with the dragon.

... Then the sound of a door opening made him look around.
Bellatrix Lestrange was striding across the lawn toward them, accompanied by Griphook. As she walked, she was tucking the small, beaded bag into the inside pocket of another set of the old robes they had taken from Grimmauld Place. Though Harry knew perfectly well that it was really Hermione, he could not suppress a shiver of loathing.
-Harry Potter and the Deathly Hallows, Chapter Twenty-Six (Gringotts).

...

Hermione sighed and set to work, muttering under her breath as she transformed various aspects of Ron’s appearance. He was to be given a completely fake identity, and they were trusting to the malevolent aura cast by Bellatrix to protect him. Meanwhile Harry and Griphook were to be concealed under the Invisibility Cloak.
-Ibid.

...

“And what do you want?”
Travers stopped in his tracks, clearly affronted. “He’s another Death Eater!” breathed Griphook, and Harry sidled sideways to repeat the information into Hermione’s ear.
“I merely sought to greet you,” said Travers coolly, “but if my presence is not welcome . . .”
Harry recognized his voice now; Travers was one of the Death Eaters who had been summoned to Xenophilius’s house.
-Ibid.

Details

  • Combatants - Order of the Phoenix (and sympathisers):
    • Hermione Granger (disguised as Bellatrix Lestrange)
    • Ron Weasley (magically changed appearance)
    • Harry Potter (hidden via the Invisibility Cloak)
    • Griphook (hidden via the Invisibility Cloak)
  • Combatants - Death Eaters (and sympathisers):
    • Travers
    • Bogrod
    • Numerous Gringotts Goblin employees
  • Outcome:
    • Decisive Order of the Phoenix Victory

Assumptions

  1. The Trio, and their fellow schoolmates closely involved in the events (e.g. Ginny, Bill and Fleur, George, etc.), are considered members of the Order as of the events of Harry Potter and the Order of the Phoenix.
  2. Assailants don't have to be killed to be considered defeated.
  3. Kingsley Shacklebolt is considered "present" at the "Attack on the Burrow" (at the wedding) via his Patronus.
  4. You are talking about Prof. Albus Dumbledore, and not his brother Aberforth.

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