Taskmaster's background is a complete mystery. His skills and photo-reflexive memory made him a masterful mercenary and target for high-profile jobs. At one point in his life he claims to have fought toe-to-toe with the Avengers.
Hired by a mysterious organization that only claimed to pay "six-figures" to see if Spider-Man was a hero worthy of recruiting, Taskmaster desired to learn everything there was about the wall-crawler. He set up recon points across New York for Spider-Man to unlock; he planted bombs on a timer for him to stop detonating, drones seeding spy-cams across the city and made him aware of mercenaries attacking executives and diplomats in order for him to stop the crimes. Therefore, Taskmaster knew all about Spider-Man abilities in stealth, traversal, combat and speed and was ready to fight.
After completing a number of challenges, Taskmaster ambushed Spider-Man and when the latter won he claimed he had much to learn about his opponent before a rematch. When all challenges were completed and Taskmaster was defeated, he revealed his intention and employers but still unimpressed by Spider-Man claimed that "some people just deserve to be poor" before escaping his webs and disappearing.
Sometimes information's worth more than money and I've learned plenty watching you
Being a contract mercenary, Taskmaster prides himself on professionalism and completing his job. Despite this he shows patience as he is not content until he has learnt everything about his target before completion and adding their abilities to his already vast skillset. Given the high-grade military nature of his equipment and recon points it’s unlikely Taskmaster is drawn by money but a desire to encounter a worthy opponent in his line of work. He appears both intrigued and enjoyed about the possibility of Spider-Man being this individual but repeatedly looks down on his own capabilities even after he was defeated by the wall-crawler, he casually implied he was not worth his client's time nor money. However, Taskmaster even praises Spider-Man completing his challenges and even attempts to teach him to improve; because of this Spider-Man jokingly claims Taskmaster to be his coach desiring him to improve as a hero albeit an insane one.
Powers and Abilities
I have a photo-reflexive memory. Anything I see you do, I can do
Photo-Reflexive Memory: Taskmaster possesses a photo-reflexive memory - all he has to do is observe someone and he is able to immediately assess and analyze their abilities, allowing him to anticipate his opponents moves in a fight. By only watching Spider-Man deal with his bombs he noticed he favored his right leg and was able to mimic his finishers by observing him in combat. Taskmaster could immediately copy Spider-Man’s swing kick, a move he claimed took years to master himself. Due to this Taskmaster was virtually untouchable in his fight with Spider-Man, his superior reflexes and memory allowed him to block all attacks, including gadgets with an almost-superhuman speed. The only reason Spider-Man was able to win was due to his enhanced awareness and speed allowed him to web and daze Taskmaster as well as the fact that he used throwables.
Swordsmanship: During his fights with Spider-Man, Taskmaster's primary weapon was a photogenic energy sword which had triple usage. It could be directly used as a melee weapon but also capable of a powerful shockwave on the ground. Taskmaster was also able to use it as a long-ranged weapon and grappling hook in combat; the grappling capabilities allowed him to copy Spider-Man's finishers and Swing Kick during their duel and even his web-shooters by using throwables in attempt to keep the fight equal.
Hand-to-Hand Combatant: Due to his photo-reflexive memory and superior training, Taskmaster is an untouchable opponent in combat. Almost any oncoming attack he can block with the exception of long-distance throws or mid-attack webs. Despite his much more muscular build and heavier weight, Taskmaster was able to perfectly match the much more agile and super powered Spider-Man's moves such as his finishers though Spider-Man was able to withstand his but this was implied to be because of his enhanced healing factor and resilience. According to Taskmaster he had fought equally with the Avengers but did not specify which one or who won.