Cyufjy

Has there been any damage incurred during a rendevouz of two spacecraft? I was reading the answer to this question and starting realizing the sheer number of things that could still go wrong even if you match the trajectories correctly and actually meet up. Has any equipment been damaged during docking procedures or has anything catastrophically failed during a docking?

Yes !

During an experimental docking manœuvre, a Progress spacecraft crashed into Mir and rendered the Spektr module uninhabitable.

On June 25, 1997, the Progress M-34 spacecraft crashed into Spektr while doing an experimental docking maneuver with the Kvant-1 module. The collision damaged one of Spektr's solar arrays and punctured the hull, causing a relatively slow leak. The crew had enough time to install a hatch cover and seal the module off to prevent depressurization of the entire Mir station. To seal the module, the crew had to remove the cables that were routed through the (open) hatchway, including the power cables from Spektr's solar panels

Several Mir crews tried to fix the leak, but failed.

The collision of Progress-34 with Spektr was the most severe.

But to complement, several minor incidents during docking occured too.

From russianspaceweb.com

March 21, 1991: Progress M-7 near miss

Following a first aborted attempt to dock, the Progress M-7 cargo ship
controlled from the ground, tried again only to zoom within meters
from the station, narrowly avoiding the collision. The rendezvous
problems reoccur as Mir crew redocks its Soyuz TM-11 spacecraft to the
rear docking port on Mir's Kvant-1 module. The problem is finally
traced to the Kurs rendezvous system onboard Mir, which has one of its
antennas missing.

January 14, 1994: Soyuz TM-17 collides with Mir

As the departing Russo-French crew conducts overflight inspection of the
station, their Soyuz TM-17 spacecraft hits the Kristall module on Mir
at least twice. Following the successful landing of the crew, the
ground processing teams discover a number of "souvenirs" taken by the
crew from the station, which exceed the weight limit allowed onboard
the Soyuz during landing. The Russian investigation team suggests that
excessive weight onboard the craft not only endangered the crew during
landing, but it could also contribute to the problems with the
attitude control system during the overflight of the station and
therefore make the collision with the station more likely

Also ISS Zvezda module's aft hatch was sligtly damaged in 2001. Expedition 3 crew conducted an inspection and removed some debris to clear it for next docking.

Link:

Dezhurov and Tyurin removed an obstruction that prevented a Progress
resupply ship from firmly docking with the International Space
Station. They also took pictures of the debris, which was a rubberized
seal from the previous cargo ship, and of the docking interface.