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Yup, personally, have to say that I wouldn't think Gollum would bother himself at all about some overzealous adventurers following him. Don't forget that the greatest huntsman of the Third Age had trouble tracking him. I don't think the companions should stand much of a chance.

Also, I think Gollum interesting himself enough in the hobbits to lead them into Shelob's den was the result of some unique circumstances. If you look at it, there's no need for him to lay elaborate traps. He has no interest but the ring. He's more than capable of escaping them. He put himself at risk in betraying Frodo to Shelob, and that's not something he does lightly.

My vote would be that they either lose him outright or are distracted by something else and then, in their absence, the trail runs cold.

Sounds like you might want to play Gollum differently . . . I guess, if I were Gollum being chased, I would want to go where it's dark, go down, into the earth, go somewhere I knew. Maybe there the adventurer's can meet something that gets in their way?

My first thought is... nice job, Spivo! I like the scene.

My second thought is that Gollum isn't really interested in the Heroes: like Deadman wrote, he got His Preciouss to think about. I think he would led his pursuer into some Orc or Spider nest (like he did with Shelob), and simply keep stealthing. I doubt he will confront his pursuer.
Not very exciting, I admit

My main worry is, though, how to inject in the encounter some... Poetry? Drama? What is the right English word?
That is a deeply significant character in Tolkien's legendarium: he could be a dark mirror of the Heroes, a tragic reminder about the corrupting influence of Power, a melancholic reminder of the humanity that can still reside even in the most wretched being...
To convey such a sentiment is a tall task, but I could not bear myself to bring in game such a character without trying to use him fully.

To be consistent with canon, adventurer's should be able to track him, see him, chase off him, but not kill or capture him. But there is a bright side of this limitation: after all, when Aragorn try to find him he had to rely on whatever he find or anything witness can say him. Aragorn is the best tracker of his age, but even him must have some material to work upon. And think about the son or grand son of an adventurer chasing the terror of mirkwood asked by Aragorn about fact from his father or grand father...

'Nasty tricksie hunters are following us. What to do precious, what to do? Gollum. Gollum.'

'We have to leave my love, we can't risk it.'

'But the tasty things we've had lately my precious...'

'I know, so juicy, so nice. But remember why we are here my love. Filthy Baggins.'

'Yes, we must leave.'

'We will have tasty things again my love.'

'Yes, yes.'

'This way, my love.'