Kennedy was outstanding on the left flank for the Dons, showing much of the trickery that persuaded Liverpool to sign him from Millwall as a teenager, and moved to centre stage to hit a stunning decider at a sparsely populated Reebok Stadium.
A foul by Andy Todd on Marcus Gayle conceded a free-kick eight yards outside the penalty area, straight on to the goal. After it had been teed up neatly for him, Kennedy curled as good a left-foot shot as you could wish to see past Jussi Jaaskelainen and into the top corner to tip this third meeting in as many years between the two sides in this competition in Wimbledon's favour.
Kennedy was instrumental in Wimbledon's first goal in a more familiar role. Bolton had made all the early running when, after 15 minutes, Jason Euell swept the ball out to him on his wing. Kennedy's accurate low cross into the area was dispatched by Gayle for his eighth goal of the season.
The highlight of the match was the contest between two left-sided midfielders, because it was Scott Sellars who threatened to turn the game for a Bolton side showing six changes from the one beaten at Queen's Park Rangers in the latest stage of their slump in the First Division.
Sellars, kept out for much of this season by a thigh injury, added a finesse to Bolton's play that often promised to give them the edge. Apart from providing a glorious early headed opportunity for Dean Holdsworth, Bolton's record signing striving hard against his old club, he also hit the post with a curling shot two minutes before the break.
The one surprise was that Sellars was not involved in Bolton's equaliser six minutes into the second half. Arnar Gunnlaugsson put over a deep cross which was won in the air by Holdsworth for Claus Jensen, one of their trio of Danes, to take on the chest and volley home from an angle.
Briefly, it looked as though Bolton were capable of going on to win, as Sellars laid on what could have been a fitting winner for Per Frandsen but his fierce shot flew just too high.
Then it was Kennedy's turn to produce what turned out to be the game's defining moment of class. Even after that, though, Bolton had their chances to take the tie into extra time. The excellent Sellars continued to create openings, with Holdsworth heading not far wide of the target.
Holdsworth skimmed the bar with another header. It was someone else who has been criticised as an expensive misfit who was destined to win it.
Bolton Wanderers (4-4-2): Jaaskelainen; Cox, Todd, Fish, Whitlow; Johansen (Taylor, 71), Frandsen, Jensen, Sellars; Gunnlaugsson, Holdsworth. Substitutes: Strong, Phillips, Elliott, Glennen (gk).
Wimbledon (4-4-2): Sullivan; Cunningham, Perry, Thatcher, Kimble; Hughes (Leaburn, 87), Roberts, Earle, Kennedy; Euell, Gayle. Substitutes: Blackwell, Cort, Castledine, Heald (gk).
Referee: A D'Urso (Billericay).Reuse content