Bash – How to Cycle Through Reverse-i-Search

Bash Reference Manual says:

Readline provides commands for searching through the command history for lines containing a specified string

You want a regexp instead of fixed string.

Try hstr:
1. Installation
2. Configuration

You should see something like this with hstr:

Update:
Another tool is fzf.

1. Install: git clone --depth 1 https://github.com/junegunn/fzf.git ~/.fzf && ~/.fzf/install

2. Re-source your ~/.bashrc: source ~/.bashrc

You should see something like this with fzf:

Your Ctrl-r is being intercepted by the kernel-based terminal cookied line processing engine.

While sleep is running, the terminal is in cooked mode, which means that the kernel-based tty line editor is working. The tty line editor supports rudimentary command line editing. The erase key (usually set to Ctrl-h (backspace) or Del) and the kill key (usually Ctrl-U) are the best known special editing keys that can be used in this mode. This line editor is useful: it's what lets interactive utilities that use neither readline nor curses to read complete lines of input from the terminal while allowing the user to make typing corrections.

But there's another special key that's active in this mode. You can see it along with the other key settings in the output of stty -a under the name rprnt and its default setting is... you guessed it... Ctrl-r. The function of this key is to repaint the current command line, in case it has become corrupted or misaligned due to other terminal output.

To avoid this, you can disable the function with stty rprnt undef.

Personally I am used to Ctrl-r being interpreted as a repaint command and I am surprised every time I try to do that in bash and it does something different!