Wanderers succumbed to their first defeat of the season with a surprise 2-1 loss at home to Macclesfield Town, who in turn collected their first victory of the campaign.
The damage was done in the first 14 minutes when Colin Daniel and Tyrone Barnett fired home spectacular long-distance efforts for the Silkmen, and the Blues spurned a number of chances before Scott Rendell's 64th minute penalty handed them a lifeline.
Kevin Betsy was tripped inside the area by Paul Morgan and Rendell sent the keeper the wrong way with a calmly taken spot-kick, but Gary Waddock's side were unable to find an equaliser despite a late spell of pressure.
Wycombe will look to return to winning ways when they travel to Waddock's former club Aldershot Town next Saturday (k.o. 3pm).
The opening to the game was overshadowed by a nasty looking injury to Jon-Paul Pittman which the striker sustained during the warm-up, enforcing a change on the subs' bench by Matt McClure.
And the thoughts of the Wanderers players may have been elsewhere in the first 30 seconds as they allowed Colin Daniel to surge forward unchallenged down the left-hand side and supply Emile Sinclair, who fired wastefully wide at the back post.
The home side looked to have recovered from their early jitters when Scott Rendell forced an excellent save from Jose Veiga at the near post after fine work from Andy Sandell, but it proved to be a false dawn as Macc stunned the hosts with a quickfire double.
Firstly Colin Daniel fired a spectacular low drive into the bottom corner of Nikki Bull's goal from 25 yards after his original free-kick had been blocked, and moments later Tyrone Barnett doubled the lead with a curling effort when given too much space on the corner of the area.
The setback stunned the Blues into life and they began to get to grips with the game, but a sea of black and yellow shirts in the Town defence made it difficult to carve open any significant goalscoring chances. In fact it only gave the visitors the chance to operate on the counter-attack, and Sinclair could have made it three when he fired over after being sent through on goal.
Wycombe were stunned, and Gary Waddock's half-time team-talk almost got much harder when Hamza Bencherif looped an exquisite lob against the crossbar from 30 yards after some excellent ball-juggling inside the Blues' half.
There was almost a lifeline on the stroke of half-time when Ben Strevens' downward header from Scott Davies' corner was well held by Jose Veiga, but Wanderers' fans were left scratching their heads when the whistle blew, leaving them facing an uphill task to get back into the game after the interval.
Club captain orchestrated a team-talk between the players before the second-half after he and Lewis Montrose came on for Keiran Murtagh and Matt Bloomfield, who was struggling with a dead leg. It gave the Blues extra impetus, and they looked more sprightly in the early stages, with Ainsworth at the heart of most moves.
After Ben Strevens headed over from the winger's cross on 51 minutes, Ainsworth started another move which ended with Scott Rendell being unable to beat Veiga in a one-on-one situation following Kevin Betsy's clever through-ball.
But luck wasn't on Wycombe's side, and the Blues were denied a route back into the game when Andy Sandell's goalbound header was deflected wide by his own team-mate Ben Strevens. But the move came from another Gareth Ainsworth cross, with the new-found width in the Wycombe team causing problems for the visitors.
Moments later, the veteran fired over the bar from Ben Strevens' cutback, but the goal finally came when Kevin Betsy was brought down in the area by Paul Morgan and Scott Rendell made no mistake in rolling the ball home from the spot to halve the deficit.
Macclesfield were rattled, but the goal only galvanised their defensive mentality and the tempo of the game then dropped. Niggly fouls all over the pitch resulted in a stop-start affair just as Wycombe needed to apply more pressure, and the luck still wasn't going the Wanderers' way - every time the nervy Jose Veiga fumbled the ball in the area, it fell to a visiting player to frustrate the Blues.
So Gary Waddock looked to Stuart Beavon for inspiration, bringing the striker on for Ben Strevens with ten minutes remaining and adding a new dimension to the Wycombe attack.
But the late rally never materialised and in truth, it was the Silkmen who came closest to finding the net in stoppage time when Nikki Bull made a fine block to deny Colin Daniel.
14.45: Jon-Paul Pittman is injured in the warm-up, with Matt McClure taking his place on the bench.
1min: CHANCE - Emile Sinclair shoots wastefully over for the visitors after a burst forward from Colin Daniel.
8mins: SAVE - Stunning one-handed save from Jose Veiga to deny Scott Rendell's effort after excellent play from Andy Sandell.
11mins: GOAL - Colin Daniel stuns the hosts with a great goal from distance.
12mins: SAVE - Keiran Murtagh's low strike from distance is comfortable for Veiga.
13mins: GOAL - Tyrone Barnett curls home in style from the corner of the area.
23mins: CHANCE - Scott Rendell ends a good move by heading wide as Wycombe increase the pressure.
27mins: CHANCE - Emile Sinclair bends a shot over the bar despite looking suspiciously offside.
43mins: CHANCE - Macc come close to a stunning third goal when Bencherif sends a volley against the bar from 30 yards.
44mins: YELLOW - Carl Tremarco is booked for a foul on Matt Bloomfield.
45mins: SAVE - Ben Strevens' header from a Scott Davies corner is well held by Veiga.
HT: Wycombe Wanderers 0-2 Macclesfield Town
HT: SUBS: Gareth Ainsworth and Lewis Montrose replace Matt Bloomfield and Keiran Murtagh.
47mins: YELLOW - Dave Winfield goes into the book for hauling down Emile Sinclair.
51mins: CHANCE - Ben Strevens nods Gareth Ainsworth's clever cross over the bar.
53mins: SAVE - Rendell's effort is too close to Veiga after a clever Wycombe move, resulting in Betsy setting the striker through on goal.
56mins: CHANCE - Danny Foster pokes wide after a mini goalmouth scramble following another Ainsworth cross.
61mins: CHANCE - Andy Sandell nods the ball towards goal but it strikes Ben Strevens and goes behind goal-kick.
62mins: CHANCE - Ainsworth spoons it over the bar from a Strevens lay-off.
64mins: PENALTY - Kevin Betsy is fouled in the area by Paul Morgan.
64mins: GOAL - Scott Rendell narrows the gap with a calmly-taken spot-kick, sending the keeper the wrong way.
69mins: SUB - Ross Draper comes off for the visitors, with Lewis Chalmers replacing him in midfield.
77mins: SUB - Sam Wedgbury replaces Emile Sinclair.
80mins: SUB - Stuart Beavon comes on for Ben Strevens.
88mins: CHANCE - Gareth Ainsworth volleys wide at the far post from Scott Davies' cross.
90+1mins: SAVE - Nikki Bull denies Colin Daniel from close range.
FT: Wycombe Wanderers 1-2 Macclesfield Town.