Able to reproduce the issue on Mac OS 10.11.6 using chrome latest Dev M55-55.0.2845.0. Observed only single entry is getting deleted from the history page when multiple entries are selected.

Can't reproduce this on tip of tree. There have been many changes to selection so one of them may have fixed this.

@Calamity : Issue is still seen on Latest Linux Build 55.0.2859.0
Attaching Video for reference

Repro Steps:
1.select any two alternate History Entries ->Click on 'Actions' Icon of selected First History Entry
2.Now select 'Remove from History' option and observe Second History is still seen checked

Deleted: OnLatest55.0.2859.0Build.ogv 1.1 MB

	OnLatest55.0.2859.0Build.ogv 1.1 MB View Download

I may be missing something here, but, I would expect the other item to still be selected because you only acted on the first item by using that item's menu. (Which I assume you can do even if you have nothing selected.)

If you used the top bar that appears when you select something (the bar that has cancel/delete) then I would assume it would delete both.

Although, the top bar with cancel/delete disappears when you delete the first item using it's menu, even though the second item is still checked, so that should be a bug.

Still can't repro this on ToT on my machine or a Windows 10 canary.

#5: Updating the selection data becomes more of a complicated mess than it's worth. I don't see this case being too common since the only purpose of selection is deletion.

#4: Can you please check this again on the latest canary? There have been recent changes to how selection and checkboxes work.

As per comment # 7 verified on latest build 55.0.2866.0 and am able to repro it.
Attaching video for reference

Deleted: OnLatestLinuxBuild55.0.2866.0.ogv 958 KB

	OnLatestLinuxBuild55.0.2866.0.ogv 958 KB View Download

calamity@: Could you please check the above attached screen-cast and update the thread accordingly. Please review the blocker label if this case should not be blocking.

Note: I could still reproduce the scenario mentioned in C#0 on Linux Ubuntu 14.04, chrome version: 55.0.2873.0 

I'm finally able to reproduce this.

Select items 1 and 3, then delete item 1 from the menu. It might be easier to reproduce on signed-out profiles, although I reproduced on both a signed-in and signed-out profile.

I think this is because by the time we try to unselect all items, the items have moved around to account for the deleted item. So we try and unselect item 3, but the selected item has moved up to position 2 and remains selected.

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/f5da8e21e5b0a869e701797c6d854519ed5416a8

commit f5da8e21e5b0a869e701797c6d854519ed5416a8
Author: calamity <calamity@chromium.org>
Date: Thu Sep 29 07:48:32 2016

[MD History] Fix item selection when deleting via menu item.

This CL fixes an issue where an item in the history list would stay
selected when deleting via the menu item with multiple items selected.
This was happening because the unselect call would trigger against
outdated selection paths.

BUG= 642665 
CQ_INCLUDE_TRYBOTS=master.tryserver.chromium.linux:closure_compilation

Review-Url: https://codereview.chromium.org/2371363002
Cr-Commit-Position: refs/heads/master@{#421773}

[modify] https://crrev.com/f5da8e21e5b0a869e701797c6d854519ed5416a8/chrome/browser/resources/md_history/app.crisper.js
[modify] https://crrev.com/f5da8e21e5b0a869e701797c6d854519ed5416a8/chrome/browser/resources/md_history/lazy_load.vulcanized.html
[modify] https://crrev.com/f5da8e21e5b0a869e701797c6d854519ed5416a8/chrome/browser/resources/md_history/list_container.js
[modify] https://crrev.com/f5da8e21e5b0a869e701797c6d854519ed5416a8/chrome/test/data/webui/md_history/history_list_test.js

Tested the issue on windows 7, Mac 10.11.6 using chrome version 55.0.2880.0.History entry unchecked after selecting Remove from History option. Please find the attached screen cast for the same.

Adding TE-Verified labels.

Note:: Issue verified on 55.0.2879.0 for Linux as the 55.0.2880.0 build got failed for Linux due to issue 652581.

Thanks,