Odd timing cover question?

[VirginiaPS13]

Car is an 89 Coupe all stock SOHCOk this maybe kinda long but its all pretty relivent to the question so...A while back my car started overheating, I checked the coolant and it appered to have what looked like rust in it. Flushed it out, it seemed like the more water i ran through the more of this stuff came out. So finally after about an hour and a half it looked better, filled up with anitfreeze and was all good for a few weeks and then it started overheating again. I decided to take the Rad. out and have it flushed, well when i took it out, the back of the rad. was rusted, so thats where it was coming from. So I flushed everything out again and got a new rad. and put it all back together. The whole time all this has been happening I have also noticed a rattle/chatter noise on start up, I figured it was a lifter since it went away when the car warmed up. Well after the new rad. everything was good again for a few weeks and it overheated again. So I decided to check the oil since its been overheating like this and it had water it in, so i figured i blew a headgasket.Fastworward to now. I have since pulled the engine, replaced the headgasket, oil & water pump, thermostat, clutch, timing kit etc.. Here is where i kinda get to my question. When I pulled the front cover on tear down one of my plastic chain guides was broke(completely gone, little pieces in the oil pan)I guess thats where the rattle was coming from. So I cleaned everything out put it all back together, back in the car. Well we started it the other night and it ran but was out of time, decided the oil pump was 180 out, went to drain the oil and water was already in it, from like 2 mins of the car being on.I talked to a guy i know and he said that if the guide broke it could have damaged the timing cover, well we took it off and sure enough it had a huge gash on the inside of the cover on one of the water passages for the pump. So my question is Would this gash in that passage allow water to get in the oil? Im trying to figure out if I had 2 problems happening at once that turned in to ONE huge PITA!
Modified by VirginiaPS13 at 9:41 AM 7/28/2009

[Vegascorbin]

Short answer: YES

There are water passeges built into the timing cover that can be dammaged when the timing chain guides brake. Head gasket was probably ok all along. Did you compresion test he engine before you did the gasket? that would have helped.

Repair or replace the timing cover (replace prefered) and clean out the oil pan (again). This should put things right.