Challenges are unlocked after clearing the story mission What's in the Box?, assigned to Spider-Man by a mysterious man known only as the Taskmaster. There are four different challenges that may be completed upon unlocking them: Bomb, Combat, Stealth, and Drone. They test Spider-Man's efficiency in completing those tasks, rewarding him with Challenge Tokens depending on his score (which is determined by his speed). Like all other tokens, he can then use them to craft suits and gadgets, though upgrading all gadgets it not required for a trophy; simply upgrade to your preferences and then spend the rest of your tokens on suits. If you do somehow manage to collect all Challenge Tokens, which this guide is meant to aid you with, then you should be able to craft all items in the game.
The use of suit powers, gadgets, and skills is especially important in these Challenges, so make sure you have a good amount of each unlocked before even attempting them. Detailed strategies are provided for each Challenge below, according to the district that they belong in. If still you don't succeed, keep in mind that practice makes perfect: memorizing a routine is crucial in all types of Challenges, especially for an Ultimate score.
Clearing five Challenges unlocks the Side Mission Fight Taskmaster: Round 1, and clearing all sixteen unlocks Fight Taskmaster: Round 2. Clearing at least one of each type of Challenge with a Spectacular score to earn four bronze trophies, and clear the two aforementioned side missions for a silver trophy.
- Bomb #1 (187 m): Perform a couple of Web Zips, then drop a bit before swinging so that Spider-Man is closer to the ground. When you reach the bomb, instead of waiting for Spider-Man to land, aim at the ground near the bomb with and zip with to the spot highlighted by a white circle. This should put Spider-Man close enough to the bomb for the + prompt to pop up, allowing him to swing the bomb away and subsequently shoot it with great speed.
- Bomb #2 (461 m): From the first bomb, zip to the top of the train and then to the top of the building in front of it using + , then burst off with and begin to swing toward the street, in the direction of the second bomb. Again, when close enough to the bomb, aim and zip to the ground beside it.
- Bomb #3 (761 m): Zip to the top of the building that stands in your path to the third bomb, and burst off with the aid of the Point Launch Boost skill. Web Zip a couple of times to reach a crane, after which you can take a long swing from it before performing two more Web Zips (this is only possible with the Quick Zip skill) to reach the next crane. After another swing, you should be able to reach the dock which the third bomb is situated on, where you can aim and zip one last time to put Spider-Man in proximity of the bomb. With this, you should obtain a score that puts you in the Ultimate range, though it may take some practice.
- Bomb #1 (349 m): The first bomb is situated not too far away, on the highest point of a roof by the edge of a building. Mix in multiple Web Zips as you swing, then when you're close enough to see the bomb, aim with and zip next to it with .
- Bomb #2 (769 m): The second bomb can be found in a park. Swing there and zip to the ground next to it after aiming to begin swinging it away as soon as Spider-Man lands.
- Bomb #3 (793 m): The next bomb is on a high building. Try to swing progressively higher as you make your way there, then simply run up the building to find yourself beside the bomb. Be careful to avoid zipping off the building at the top; a slower and deliberate approach is recommended here.
- Bomb #4 (1073 m): From the third bomb, zip to the edge of the building and press upon landing for a boost toward the fourth bomb. This one is also on a building, though the intricate architecture makes it difficult to climb. Use a big swing to reach as high a point as possible, then zip to an edge of the building close enough to carefully approach the bomb. Toss it to complete this challenge.
- Bomb #1 (229 m): As soon as the challenge starts, turn toward the direction of the closest bomb and start using Web Zips to put Spider-Man in range of the edge of a building in front of him. Zip to it and use Point Launch Boost to gain a burst of speed, then utilize some more Web Zips to place Spider-Man above the roof that the first bomb is located on. Aim and zip to a spot right next to the crate, then strike it open with to reveal the first bomb. You can also utilize a Ground Strike when above the crate in order to smash it from a distance, though this must be aimed properly and may take more time.
- Bomb #2 (323 m): You should now be a short distance away from the second bomb. Swing to the lower roof that this bomb is located, and zip into position next to it to swing it away.
- Bomb #3 (465 m): The third bomb will be a bit further than the second, but it should still be reached fairly quickly. This one is located on the ground inside a bag; you must first pull the bag off of the bomb using + before swinging the bomb away.
- Bomb #1 (210 m): Reach this bomb however you wish, whether using swinging, Web Zips, point launches, or some combination of the three, as long as it ensures a high swing toward the roof of the building which the first bomb is located on. Zip into position next to the bomb to toss it quickly and begin moving toward the second.
- Bomb #2 (457 m): From the first bomb, zip to the edge of the building facing the second bomb and press for a boost toward it. This bomb is also located on a roof, so be sure to keep your Web Zips and swings high, allowing Spider-Man to zip next to it quickly.
- Bomb #3 (510 m): This third bomb is once again located on a roof, and can be reached just as the others were reached: maintain a high altitude and zip into position next to it to swing it away. Overall, this is one of the simpler bomb challenges, and should be completed with ease as long as a proper routine is practiced.
Equip Web Bombs immediately and begin tossing them at enemies. Use Web Shooters to stick webbed up enemies to the car and the wall, striking the enemies toward them if you have to. You can also knock enemies down with an air launch and then web them to the ground with Web Shooters. Once the next group arrives, equip the Electric Web or Spider Drone to stun the enemies, softening them up for basic strikes. You can also use Trip Mines to string the enemies to the walls.
For the third group, re-equip Web Bombs and toss them so that all members of the tightly-knit group are webbed, then equip Web Shooters once again to web them to the walls or to the ground after knocking them down. The final two enemies are located up high on the opposite side, wielding rocket launchers. Use a web strike to zip to them, then knock them to the ground with air launches before webbing them to the ground with the Web Shooters.
Use Trip Mines to stick some of the enemies that rush toward you together, neutralizing a good number of them. Equip Web Shooters and use air launches to knock the remainder of them down, then web them to the ground. Head toward the next group (you can locate them on the mini-map) and use an Electric Web or Spider-Drone to stun them, softening them up. You can then use Trip Mines to web them together or again, knock them to the ground and fire Web Shooters to stick them there. Overall, as long as you use your gadgets often, the relatively small number of enemies in this challenge should be handled easily.
Equip Web Shooters immediately to begin webbing enemies to cars and walls, and the ground after knocking them down with an air launch. Use any finishers that you obtain on some enemies that are more difficult to knock down, such as those with stun rods or shields. Use Web Bombs and Electric Webs on clusters of enemies before webbing them to walls or the ground with Web Shooters, as well as using Trip Mines to web them together. This may prove difficult as the enemies are spread across a wide area, so make sure to catch the groups as they rush out of the building and cars before they spread out.
For any enemies left over, use Web Strikes to reach them (the Long Strike skill may be necessary here) and air launches to knock them to the ground and web them there. Lastly, use any leftover finishers to complete the challenge in good time. Even if you don't have many gadgets or upgrades unlocked, this challenge is entirely doable with the Web Shooter strategy.
Equip Trip Mines to begin tackling the enemies in the center of the area, webbing them to walls and to each other. Once you run out of Trip Mines, switch to Web Shooters and web any remaining enemies to the ground or walls. You can also use any grenades that are thrown by the enemies against them, tossing them back to stun them and allowing you to perform some air launches that will then allow you to web them to the ground. For the shielded enemies, use finishers to rid yourself of them quickly, or a Swing Kick to stun them and then web them (the Swing Kick and Buster Bunker skills are necessary for the latter strategy).
Once the center group is defeated, zip to the outer edges of the area, where you should see some enemies rushing in on the mini-map. Use Swing Kicks and air launches to knock the enemies down here, then use Web Shooters to web them to the ground. Return to the center area to find even more enemies rushing in, for which you can equip a crowd control gadget such as the Web Bomb or Electric Web to stun them. You can then use Trip Mines to finish them off, webbing them to the environment and each other.
Return to the outer edges of the area to deal with the last group of enemies, consisting of gunmen. Again, utilize air launches and then web them to the ground to deal with them as quickly as possible. Using this strategy allows for some room for error, so as long as you perform well enough against all groups, you should earn an Ultimate score.
Upper West Side
From your starting position, look to the roof ahead, where two guards can be seen. Zip to the floodlight there and take down the one to the left immediately, as the other is focused on the space in front of him. Take down the other, and then zip to the high roof up ahead, to the left. A sniper can be seen shining a flashlight here; since he's isolated, he makes an easy target. Another sniper past this one is also isolated, making for another easy takedown. Swing to the roof of the building on the opposite side of this area to find two more isolated snipers. Take them down to shift your focus to the five remaining enemies on the ground.
Take down the guard walking by himself in the center of the area. Another guard should be walking by himself to the right, and can also be taken down easily. From here, you can transition to the man standing guard over the hostage, taking him down before he can fully realize the danger that he's in. Take down the guard on a porch overlooking this area, and then zip to the roof to the left to find the final enemy (you can locate him on the mini-map if need be).
Upper East Side
Start by taking out the closer guard on the low roof in front of you. The other guard should continue walking by obliviously; take him down, then zip up to the roof of the building he was walking by. There are two guards here: a sniper past the water tower and a gunman keeping watch over him. Take down the gunman keeping watch first, then the sniper. On a lower roof directly beside this one is another guard walking by, who you can also take down. This should leave five enemies to neutralize.
Climb back up to the roof where the sniper was, then zip to the roof past this one, higher up, where a lone guard can be found with a hostage. Take down the guard, then make a left turn, climbing over the two sets of bushes keeping you from a sniper. Take him down, then zip up to a higher roof of this same building. The final three enemies can be found here. Take down the one standing in the center, then the one to the left, then finally the one standing over the edge of the building to the right. This may take some luck, as these enemies will occasionally walk into each other's sight, but even if one becomes slightly suspicious, you can take him down before he realizes that he should alert the others.
Zip to the closest floodlight and then zip to the one straight ahead of it to take down the lone guard on the raised platform. Another guard will be walking by this platform on the ground, and can also be taken down without notice from his colleagues. Zip up to the stack of garbage to the right and take down the guard on the other side of it. This leaves only four enemies.
Zip back to the floodlight on the platform where the first enemy was taken down. Down on the ground to the left of this platform are two more guards that can be taken down, out of sight of each other (though they will walk toward each other occasionally, so make sure to look for the "safe" indicator). Zip back up to the very first floodlight you zipped to, which is nearby a raised platform on the edge of the compound. There are two enemies here; fire a shot from the Web Shooters toward the edge of the platform to distance one from the other. Take down the guard that stands his ground, then the one that was distracted by the shot, as he'll have his back turned to the other.
Hell's Kitchen (port)
This stealth challenge is also in Hell's Kitchen, though it can be found on the edge of the city. The area that it takes place in is also much wider, making for a more difficult challenge. Start by turning your attention to the right of the area, where a lone guard can be found walking beneath a catwalk. Take him down, then zip up to the catwalk and take down the sniper there. Two snipers on the opposite catwalk can also be taken down quickly, as well as an enemy on the ground nearby and another by the floodlight in the center of the area.
Zipping back up to the second catwalk and then the roof above it, take down two snipers. To the left of this building (facing the center of the area) on the ground, take down another lone guard. This leaves two enemies; one beneath the second catwalk and another walking around the center of the area. Take them both down while on the ground to complete this challenge in good time.
- Use Web Zips and low swings to follow the drone closely as it makes a turn above the expressway and drops the first bubble. Under a glass bridge connecting a building is where it drops the second, so again, make sure to swing low and utilize the Quick Zip skill.
- After the first two bubbles, begin to transition to higher swings. It drops the third bubble on the roof of a building. Use Web Zips to maintain this altitude, as it drops another bubble on the roof of a building at a similar height.
- The fourth bubble is dropped on the roof of a police building. Afterward, the drone makes a slight drop and leaves a bubble by the side of a building. Swing close without making contact with the building, as running on the wall will require you to dismount, thus losing time.
- The drone then trends upward, and so should your swings. The sixth bubble is dropped up high between buildings, and the seventh and eighth are dropped above buildings, with the eighth placed neatly on a spire.
- Following the bubble atop the spire, run up the tall building directly in front of you, using to zip upward. The drone drops a bubble here, and then arcs down to the other side of the building upon reaching the top. Use at the top of your climb to swing from the roof to the other side of the building, where you can drop into the tenth bubble.
- The eleventh bubble is located on a low roof between two taller roofs. Use a Web Zip or low swing to reach it upon dropping, then drop further as the drone makes its descent. Watch for the prompt to zip toward the drone, which saves time versus waiting to land.
Upper East Side
- Follow the drone as it drops the first bubble beneath a bridge that connects one side of the building to the other. It loops around the right side of the building after this, but you can continue straight under the second bridge, as it drops the second bubble on the roof of a building straight ahead. Make sure to swing high to reach it.
- Use Web Zips to maintain your altitude above the roofs as the drone drops the third bubble atop a billboard, then make a turn and swing low as it drops the fourth bubble beneath a bridge.
- Swing between buildings, then make a right turn on the street, as the drone drops a bubble at the corner of a building before making another turn. The fifth bubble will also be along this street, albeit a little lower, as well as the sixth by a building to the left.
- For the seventh bubble, the drone makes a right turn and drops its height. For the eighth, the drone zig-zags (left, then right) and flies high above the roof of a building. Swing high and release at the height of your swing in order to gain a tremendous amount of altitude, allowing you to drop onto the eight bubble.
- Continue to swing high, as the drone drops low to trick you into following before flying high once more, dropping the ninth bubble atop the roof of a tall building. Continue straight as the drone turns and use Web Zips to reach the tenth bubble, atop a building straight ahead.
- Drop after the tenth bubble, just as the drone does, to drop onto the eleventh bubble just as the drone produces it (atop a muddy construction site). Begin to swing high again for the twelfth, thirteenth, and fourteenth bubbles, all located above buildings. The drone also lands on top of a building.
- Swing low and use Quick Zips to follow the drone from the start, as it drops the first bubble right above a lamp lower than your starting position. The second bubble is then to the right of a raised building, on the roof of another.
- The third bubble is beneath a raised building, requiring you to swing low beneath it. The fourth bubble is also dropped here before it makes its exit and drops to street level.
- Swing low to follow the drone beneath the bridge, where it drops a fifth bubble. Run up the building that the drone climbs and press at the top to fly into the sixth bubble, then again to fly into the seventh.
- Drop down to follow the drone along the bridge, where it drops the eighth bubble beneath a crane, then follow it as it makes a right turn between some buildings and swing into the ninth bubble.
- The drone then makes a left turn, dropping the tenth bubble beneath another bridge, followed by a right turn, dropping the eleventh bubble slightly higher between some buildings.
- Swing higher as the twelfth bubble is dropped atop a light, then lower as it drops the thirteenth on the pavement straight ahead. Web Zip forward to catch the drone on the roof of a building, concluding the challenge.
- Swing straight ahead to follow the drone until it makes a right turn, after which you can drop slightly as you continue following it. It drops the first bubble above some trees, then the second bubble after zig-zagging some buildings.
- The third bubble is dropped along a straight path following the second, and the fourth is dropped as the drone drifts left, above a billboard.
- Swing high as the drone makes a right turn, as it drops the fifth bubble atop a tall radio tower. You can then drop a bit as it drops the sixth bubble atop a low roof, then drop even further as it drops the seventh and eighth bubbles along the ground.
- Upon picking up the two lower bubbles, run up the building to follow the drone's path, though it may be best not to press upon reaching the top here, as you may swing right past the ninth bubble, sitting atop the roof.
- Swing lower for the tenth bubble before making a turn. The drone lands atop a building, allowing you to catch it with as you approach.