The Hill sphere radius of Pluto is about $r$ = 6 million km. Most of the Kuiper belt is in prograde motion around the Sun (like Pluto). Pluto's average speed is under a lazy 5 km/s for an orbital period of about 248 years. If the difference in orbital speed between Pluto and an average KBO is just 1 km/s, then Pluto will "sweep out" $\pi r^2 *86,400s *1km/s = 9.8 \times 10^{18} km^3= 2.9 \times 10^{-6} AU^3$ of the Kuiper belt per day.
The Kuiper belt is described as a donut extending from 30 to 55 AU. The volume $V$ of a torus is $V=2\pi^2Rr^2$, where $R=42.5$ and $r=25$ are the major and minor radii, so the approximate volume of the Kuiper belt is $5.24 \times 10^{5} AU^3$. Of course, KBO's are distributed more densely near the center of the torus, and exist increasingly rarely outside the torus.
So, Pluto might sweep out about $V_1 = 2.9 \times 10^{-6} AU^3$ of the $V_2=5.24 \times 10^{5} AU^3$ volume Kuiper belt per day. That means there would have to be approximately $V_2/V_1 \approx 1.8 \times10^{11}$ (or 180 billion) total objects in the Kuiper belt for one to enter into Pluto's Hill sphere each day, on average. It might even need to be much higher since Pluto's orbit is more inclined then the distribution of the Kuiper Belt, as shown here:

We only know of about 2000 KBOs according to this NASA site. Pitjeva and Pitjev postulate only millions of objects in the Kuiper belt, so it may be unlikely that many KBOs enter Pluto's Hill Sphere radius each day.