Littler won the bull-off against Woodhouse and had the crucial advantage of throwing first in the short format.
He even secured a break in the first set to move 3-1 ahead and appeared to be on course for the last 16.
However, the world number one, whose bid for a perfect major year had already been ended at the World Series of Darts Finals, could not complete a clean sweep.
Woodhouse held his throw to level the match – and kept the momentum going without a pause.
After neither player could win the opening leg of the third set, “Woody” took control and broke in the very first leg. Littler missed six darts at 54 to break straight back and was given no further chance to get back into the match.
Van Gerwen throws away lead against Joyce
Van Gerwen experienced a similar match earlier on. The Dutchman, the second most successful player in the history of the tournament behind Phil Taylor (11) with six titles, won the bull-off and the first set, just like Littler.
The standard was not high from the outset, but the contest was evenly matched.
The advantage of throwing first was repeatedly evident, as “Mighty Mike” got the chance to go for similar checkouts before Joyce.
The match turned after the break, as van Gerwen completely lost his way on the doubles. Although he failed to reach the first visit only once in the second set, he missed no fewer than 14 darts at checkouts. Joyce, who was trailing in the scoring, was able to fight back and hit three of his five doubles.
The decider then swung back and forth. Van Gerwen dropped both of his throw legs, while Joyce dropped only one. That gave the advantage of throwing first to the Englishman, who checked out for the match after his opponent missed bullseye.
Springer loses to Noppert
Niko Springer has once again failed to progress beyond the first round of the World Grand Prix. In the first match of the day, the “Meenzer Bub” lost 2-1 to Danny Noppert in Leicester.
Springer struggled particularly with the doubles at the start of each leg. The notoriously demanding double-in, double-out format repeatedly meant that, despite throwing first, Springer was the second player to get on the scoreboard. Noppert, by contrast, rarely needed two visits to find a double.
Noppert therefore secured a break in Springer's opening throw leg to move 2-0 ahead, checking out 112 in the process. “Freeze” held his throw to take the set and then started the second set with another break.
At 2-1 in the second set, Noppert had his first match dart but missed it and was broken straight back. Springer held his throw and forced a decider.
Springer faltered again on the check-in, though. Throwing first in the second leg, it took until the eleventh dart to find the target. The 26-year-old celebrated sarcastically towards the crowd, which Noppert acknowledged with a shake of the head before copying him later.
The result proved him right: just as he had won the first, the Dutchman also took the third set 3-0. In a leg-based format, this match would have finished 8-3 – a better reflection of how it unfolded.
Plenty of tight matches
There were no further surprises on Monday evening; however, many matches went the full distance. For one, Gerwyn Price beat Sebastian Bialecki 2-0, while Wessel Nijman defeated Rob Cross 2-0. In the second Welsh-Polish clash, Jonny Clayton beat Krzysztof Ratajski 2-1.
World Series winner Ross Smith managed to beat Cameron Menzies 2-1. Nathan Aspinall also beat Kevin Doets 2-1.