Yes there are 3 drain plugs, each 1 is for either the engine, transmission & primary. If you are doing a scheduled oil change, change all 3. I also have an 08 Superglide, even though the book that comes with your bike says to replace transmission & primary at different intervals to the engine, I find it better to do all 3 at the same time, it may cost a little more but your bike will love you for it.
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Sorry I do not have the expertise from this vintage but I am surprised not one else has responded. The transmission drain will be on the bottom of the transmission, usually in the middle and a 5/8 inch hexagon plug with a 1/4 inch Allen socket in the middle which is useful on Softail as the plug is in between the shock/springs and not easy to take off and put on with an ordinary socket and wrench as it is somewaht offset to one of the shock/spring assemblies and a medium long 1/4 inch ball Allen wrench is most useful there. The oil fill is likely a 3/8 inch allen plug on the front of the clutch release cover on the right side of the bike.
Way underneath the bike, sort of near the kickstand, is the drain plug. You really have to get underneath to see it. Unscrew that and let the oil drain into a container, then replace the plug and tighten. Under the triangular silver cover on the right side of the bike is the oil filter. Unscrew the three bolts and take the cover off, and be careful not to lose the spring under the oil filter. Replace the oil filter with a new one and make sure the spring is situated correctly. You may want to replace the rubber o-ring for the cover too.
Replace the oil with SAE 10w-4o and check the sight-glass for proper level.
On a Dyna model after about the year 2000 the engine oil drain will take a 5/8" wrench to remove and it faces the front of the bike, there is also a identical drain plug for the transmission that faces downward. Most dyna models take around 3 quarts of engine oil and about 22 ozs. of transmission oil.
There should be a drain plug on the trailing side of the slider. Some have cross point screwdriver heads on the plug others have allen or hex head plugs. Remove the plug and work the forks up and down. If all fails, you can remove the entire tube and turn it upside down.
The primary on all late model bikes (1985 and later) are known as "wet primaries" because they have their own lube in them. The newer bikes like yours came with H-D's Syn3 20W50 oil in the primary.
To change the oil, stand the bike up as straight as safely possible. Remove the derby cover. You'll see the clutch assembly. Notice the outer clutch drum is made of aluminum. Inside that is a black disc. This is the clutch diaphragm spring.
To drain the primary, remove the drain plug at the rear of the primary on the bottom. Replace the drain plug and refill the primary with oil until it's just to the bottom of this diaphragm spring. Usually 38-44 ounces. Do not overfill as too much oil will make your clutch drag.
remove the drain plug from the oil pan, you will need either a 3/4" box wrench or a 5/8" box wrench and the drain plug will be facing forward on the the oil pan. It is easiest to remove this drain plug from under the right side of the bike. put drain plug back in after about 10 m,inutes of drain time and tighten to 18 ft. lbs. Dont forget to change the oil filter as well.
Since a Dyna's oil tank is on the bottom of the transmission, so is the drain plug. There are two drain plugs. The one on the left side is the oil drain. The one closer to the center is the transmission drain plug.