I'm assuming this photo was taken during the 1990 season, in which Dascenzo played in four games against the New York Mets that also included Tim Teufel. I'm not sure if Dascenzo was trying to steal second or what, but I'm going to try to figure it out.
In Dascenzo's first game against the Mets at Wrigley Field in 1990 (JUNE 12), he entered the game in the top of the 9th as a relief pitcher. The Mets were winning 19-6 so Dascenzo probably couldn't have done much worse than anyone else the Cubs trotted out that day. In fact, he went three up, three down. He did allow a hit to future Cub Dave Magadan, but got Tim Teufel to ground into an inning ending double play. Could that have fueled Teufel's diving attempt to tag Dascenzo out?
According to the boxscore for the bottom half of the inning, Dascenzo led off with a single. That was followed by a ground ball up the middle by Curt Wilkerson, advancing Dascenzo to second. I can easily see this play as Dascenzo rounding too far off of second and having to dive back in after the center fielder came up throwing.
Let's take a look at the other three games though to see if there's anything there.
In the next game (JUNE 13), Dascenzo was on base twice. The first time he walked but the inning ended without him advancing to second or being involved in a play at the second. In his next at bat, he doubled with a line drive to short LF-CF. I take "short" to mean this was one of those hustling doubles that was stretched from a single. The photo could easily be that play too because if the ball was hit to the left side, the shortstop would be the cutoff man and the second baseman would be covering the bag.
A few weeks later (SEPTEMBER 21), the Mets come back to town. Doug Dascenzo enters the game as a defensive replacement for Derrick May in left field but is pinch hit for when his turn to bat comes around. Tim Teufel was playing first base that day anyway as Tommy Herr played second. Not that a first baseman can't cover second, but Dascenzo didn't bat or pinch run so its a moot point.
In the fourth and final match up at Wrigley Field that included both Doug Dascenzo and Tim Teufel (SEPTEMBER 24), Teufel entered the game late as a pinch hitter and never took the field. Another moot point.
So the choices are revenge tag attempt on an overrun base (safe) or a hustling double (also safe). What say you?
If you like this kind of breakdown stuff (and shameless self promotion), check out my 2014 Topps Blog where I am doing something similar for all of the cards in the 2014 Topps set on a daily basis.