If you go to https://www.historicaerials.com/viewer
and look at the 1919 and 1947 topo maps, you see in 1919 the Freehold line crossed the NY&LB over to the Highlands line (presumably at grade). The details of the connections to the NY&LB are difficult to see because of the "watermark", but by clicking at the other old maps there it seems the connections were such that from Freehold you could connect directly in the direction of Jersey City, as one might expect . For Highlands, it's hard to see because of the watermark - but it sort of looks like in 1919 that you have to travel across the NY&LB to the Freehold side and reverse. Or the map was just not complete.
By 1947 there was a wye on the (compass) south side of the NY&LB leading to Freehold, and a connection in one direction to Highlands, with no crossing of the NY&LB any more. The Freehold line has a slight kink from its former alignment to lead to the new wye.
Some more detail is in an employee turntable at http://raildata.railfan.net/cnj/homecnj.html
. Look at the first NY&LB page. Regarding orientation, at Matawan, up would be in the direction of Freehold (note the wye) and down would be towards Highlands. But I don't know the date of the timetable - I would assume 50's or 60's
(The terms east and west are confusing here, since while travelling RR westbound on the NY&LB you are actually going compass east!)