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Although he's well-regarded as a military leader for having retaken Jerusalem from the Crusaders in 1187, Saladin's military career was not without its setbacks. Richard the Lionheart handed him a couple of defeats during the Third Crusade, for example, though ultimately that crusade failed to achieve its goal. There's also the 1177 Battle of Montgisard, in which Saladin's first attempt at capturing Jerusalem was decisively ended in what is now central Israel by an outnumbered Crusader army under King Baldwin IV.
Baldwin, by the way, is one of the most remarkable of all the Crusaders in my humble opinion—after all, they didn't call him the "Leper King" for fun. That he survived long enough to rule Jerusalem at all is pretty incredible; that he not only ruled, but was able to lead (successful) armies in the field is really astounding.
Just how badly the Christians were outnumbered at Montgisard is anybody's guess, because medieval sources only count the number of knights in Baldwin's army, and that only amounted to something shy of about 400 men, many of them Knights Templar. Obviously Baldwin didn't defeat Saladin's army, variously listed at anywhere from around 8000 to 26,000 men, with 400 guys, and we know that medieval European armies included lots of fighters who were not knights, but nobody bothered to count those fighters in this case. Still, it seems likely that they were, in fact, pretty significantly outnumbered. They were so badly outnumbered that when Baldwin had previously attempted to stop Saladin's march toward Jerusalem at Ascalon, Saladin simply detached part of his army to occupy Baldwin and kept right on marching.
"The Battle of Montgisard," by 19th century French painter Charles-Philippe Larivière; note Baldwin directing the battle from his litter, which seems not to actually reflect what happened (Wikimedia Commons)
In fact, Saladin's overconfidence about the size of his own army seems to have been part of his undoing. Instead of making a beeline for Jerusalem, which was obviously the main prize both from a tactical and religious standpoint, he decided to take his time and nab a couple of the towns and fortresses along the way. Meanwhile, Baldwin was able to shake free of the troops Saladin left at Ascalon and go after the main body of the Ayyubid army. The two forces met somewhere near Ramla, a strategically important point that sat at the crossroads of the Cairo-Damascus highway and the main road from Jerusalem to its port at Jaffa (today it's an Israeli city of about 70,000 people).
Saladin was preoccupied trying to dislodge his baggage train from a muddy patch, and the arrival of Baldwin and his army apparently took him totally by surprise. His army was scattered all over the place, some working on the baggage train and others out foraging for supplies and raiding in the countryside. Baldwin was no dummy, so there was no "let's do the honorable thing and wait for our enemy to get ready before we attack" nonsense—he ordered his men to attack immediately. We're told that Baldwin, as weakened as he was by his condition, fought right alongside his men, which, as it would for Henry V at the Battle of Agincourt in 1415, had an inspiring effect on his army.
Saladin managed to hop on the back of a fast camel and make a break for it, but his army was cut to pieces. His losses can't be accurately measured, but estimates are that he brought about one tenth of his army back to Egypt with him, and while some of the 90% he lost may have been due to desertion, I think it's safe to say that the vast majority were killed. Unfortunately for the Crusaders, Saladin's position in Egypt and Syria was a whole lot stronger than theirs in Jerusalem and the other Crusader states, and it only took him a couple of years (until 1179) to build up a new army and start harassing the Crusaders again. In 1182 he launched a new campaign to capture Jerusalem. Baldwin finally succumbed to his illness in 1185 and was eventually succeeded by a much less capable king, and as a result Saladin's efforts finally proved successful.