Skippers Martin Bennett and Eddie McDonald are both confident of victory ahead of the final Rutland derby of the year on Saturday.
Oakham beat Uppingham 1-0 when the sides met early in the season but there is more than just county honours at stake when the sides meet at Tods Piece.
Uppingham’s Bennett said: “This will be the biggest game of the season so far.
“We are the only two Rutland sides in the Peterborough League’s top division and it’s nice to play when we are both near the top.”
Bennett expects a good crowd on the sidelines on Saturday for a match that been an evening fixture for many seasons.
“This is better,” he said. “Hopefully there will be quite a few people down to watch.”
After a great start to the season, United have endured a tough couple of months picking up just one victory in eight matches while a win for Town would lift them to within three points of fourth-placed Oakham.
The Town captain added: “They had a good start but we have caught up a little.
“Form in derbies can mean nothing but I don’t think there is anyone expected to be missing from our side - I think we’ll win it.”
Up the A606 at Oakham, McDonald is equally bullish about his side’s chances of completing the double.
The United skipper said: “A win over a rival always means a lot.
“It’s the one we picked out from the fixture list at the start of the season.
“It’s a shame that we have trailed off in the last few weeks but if we can beat them it can restart our season.
“Over the last couple of weeks we have started to play better. I think we are good enough to beat them.”
United’s dip in form coincided with suspensions and an unsettled side but McDonald says United are returning to full strength with the influential Jamie Forbes, who was missing for last weekend’s draw at Stilton, returning this week.
For Uppingham a win would provide a massive boost ahead of a series of tough fixtures in January. Kick off at Tod’s Piece will be at 2pm on Saturday.