I used to have a TH350... where the speedo cable screws on, always loosens up and leaks oil. Open that up, pull out the little plastic speedo gear and check if it's good. Check the end of the cable, see if the needle is straight and check for damage. If it's all good, push some sealant on the threads and screw it back on tight. If not, try getting a gear or cable.
If you have a Y pipe, you have a crossover pipe... you might have oil dripping on the crossover pipe from the following places...
rear main seal (back of oil pan), transmission (sounds like your speedo cable), oil filter, or back of valve covers...
Start the car, get it up to temperature, then rev it a few times to get the oil pressure up... then check for the leak from the engine. If it's not from the engine, go for a short drive, get it up for 30 or 40mph, then stop and check the speedo cable at the transmission... see if any oil dripping out. Check the trans oil pan also.
did you check the dipstick tube?