Pioneer vsx-305 need wiring diagram for this connection to the HTP100-SW (Subwoofer) & 5 surround sound speakers

If you wish to get some details; check the site linked here. Pull up older posts.
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http://www.martinlogan.com/pdf/manuals/manual_descent_i.pdf

The front speakers go into the sub in the two bottom inputs from the receiver. the two upper are outputs to the actual speakers,SOYOU RUN RUN THE FRONT SPEAKER WIRES FROM THE RECEIVER TO THE INPUT OR LOWER CLIPS ON SUB,THEN RUN WIRES FROM THE OUTPUT OR UPPER CLIPS FROM SUB TO THE FRONT SPEAKERS.

If you are referring to 5.1 surround you would have to have 5 speakers plus one powered subwoofer. The front left and right as well as your center channel to the majority of the sound reproduction with the rear channel being there for intricate sounds and background noise. The subwoofer will be a preamp output from your receiver. That signal will then get amplified by your subwoofers power amp. Generally subwoofers are tucked away in a corner while the other 5 speakers form a box around your viewing area.

Test with an surround sound media ie. Blu-ray or DVD)_. Disconnect the front and all other speakers that are working to see if sound from the missing speakers are heard. If this doesn't work then start by tracing and checking all the wires from the receiver to the speakers for bad/shorted/open connections.

PLEASE VOTE IF THIS WAS HELPFUL. THANKS & GOOD LUCK.

Make sure that the sound field/programme you have selected is dolby digital not stereo.(On the amp)
You also need to check on the display that is says DIGITAL not ANOLOUGE, as only a digital input, Optical fibre cable, HDMI, COAX will be a digital signal.
If you are using red and white rca connectors, it is not going to work, as this is an Anolouge signal.

The original Pioneer subwoofer has its own amplifier built in to the speaker, so the only cable required on the original speaker is a single RCA cable. To connect a different brand subwoofer to the Pioneer you will have to make sure that you have a subwoofer with the same specs. It will need its own built in amp to work, as you can only connect it with one RCA

Rear Surrounds are not supported on this unit, they would be the 6th and 7th channels in a 7.1 rig. I think you mean Surrounds (channels 4 and 5 in a 5.1 rig).

Lets ponder: How is there any relationship between Surrounds and your separately-amplified Subwoofer? I don't see it, unless you inadvertently chose OFF for the Sub definition when you were in the Speaker selection menus adding the Surrounds. Look again.

Based upon your description, the subwoofer is just a speaker and is taken from the normal speaker outputs. Run your A channel to the sub and then from the sub to the left and right front speakers. That should do it.
Dan